Abstract
This chapter discusses the various methods for the preparation of oxabicyclic compounds, with an emphasis on the stereo- and enantioselective synthesis of these substances. Methods to desymmetrize meso oxabicyclic compounds are also presented. The utility of these substrates for organic synthesis is demonstrated by the many strategies available for ring-opening the bicyclic compounds to yield cyclic and acyclic structures. Examples demonstrating how this strategy has been incorporated into the efficient syntheses of many natural products are presented.
Preview
Unable to display preview. Download preview PDF.
Abbreviations
- 9-BBN:
-
9-borabicyclononane
- BINAP:
-
2,2′-bis(diphenylphosphino)-1, l′-binaphthyl
- Bz:
-
benzoyl
- COD:
-
cyclooctadiene
- dba:
-
dibenzylideneacetone
- DDQ:
-
dichlorodicyanoquinone
- DIBAL-C1:
-
diisobutylaluminum chloride
- DIBAL-H:
-
diisobutylaluminum hydride
- DMAD:
-
dimethylacetylene dicarboxylate
- DME:
-
dimethoxyethane
- dppb:
-
1,4-bis(diphenylphosphino)butane
- HMPA:
-
hexamethylphosphoramide
- LAH:
-
lithium aluminum hydride
- LDA:
-
lithium diisopropylamide
- LHMDS:
-
lithium hexamethyldisilazide
- LiDBB:
-
lithium di-tert-butylbiphenylide
- mCPBA:
-
meta-chloroperoxybenzoic acid
- MS:
-
molecular sieves
- PMB:
-
p-methoxybenzyl
- PMP:
-
p-methoxyphenyl
- PPTS:
-
pyridinium p-toluenesulfonate
- pyr:
-
pyridine
- Red-Al:
-
sodium bis(2-methoxyethoxy)aluminum hydride
- TBDMS:
-
tert-butyldimethylsilyl
- Tf:
-
trifluoromethylsulfonyl
- THP:
-
tetrahydropyran
- TMP:
-
2,2,6,6-tetramethylpiperidine
- TMS:
-
trimethylsilyl
- Tr:
-
trityl
- Ts:
-
toluenesulfonyl
References
Lipshutz BH (1986) Chem Rev 86:795
Moore JA, Partain EM (1983) J Org Chem 48:1105
Nugent WA, McKinney RJ, Harlow RL (1984) Organometallics 3:1315
Bailey MS, Brisdon BJ, Brown DW, Stark KM (1983) Tetrahedron Lett 24:3037
Moursoundidis J, Wege D (1983) Aust J Chem 36:2473
Laszlo P (1986) Acc Chem Res 19:121
Ipaktschi J (1986) Z Naturforsch Teil B 4:496
Saksena AK, Girijavallabhan VM, Chen Y-T, Jao E, Pike RE, Desai JA, Rane D, Ganguly AK (1993) Heterocycles 35:129
Dolata DP, Bergman R (1987) Tetrahedron Lett 28:707
Matsumoto K, Sera A (1985) Synthesis 999
Sargent MV, Dean FM (1984) Furans and their Benzo Derivatives, (ii) Reactivity. In: Katritzky AR, Rees CW (eds) Comprehensive Heterocyclic Chemistry, vol 4, Pergamon Press, Oxford, p 599
Shipman M (1995) Contemporary Org Synth 2:1
Vogel P, Fattori D, Gasparini F, Le Drian C (1990) Synlett 173
Reymond JL, Vogel P (1990) Asymmetry 1:729
Vogel P (1990) Bull Soc Chim Belg 99:395
Carrupt PA, Vogel P (1984) Tetrahedron Lett 25:2879
Carrupt PA, Vogel P (1988) J Phys Org Chem 1:287
Black KA, Vogel P (1984) Helv Chim Acta 67:1612
Vieira E, Vogel P (1983) Helv Chim Acta 66:1865
Kernen P, Vogel P (1993) Tetrahedron Lett 34:2473
Takayama H, Iyobe A, Koizumi T (1986) J Chem Soc Chem Commun 771
Takahashi T, Namiki T, Takeuchi Y, Koizumi T (1988) Chem Pharm Bull 36:3213
Corey EJ, Loh TP (1993) Tetrahedron Lett 34:3979
Evans has recently shown that a cationic bis (oxazoline) Cu(II) catalyst is effective for the enantioselective cycloaddition between furan and acryloyl oxazolidinone, Evans DA, Barnes DM (1997) Tetrahedron Lett 38:57
Yamamoto I, Narasaka K (1995) Chem Lett 1129
Roush WR (1990) Stereochemical and Synthetic Studies of the Intramolecular Diels-Alder Reaction. In: Curran DP (ed) Advances in Cycloaddition, vol 2, JAI, Greenwich, p 91
Craig D (1987) Chem Soc Rev 16:187
Taber DF intramolecular Diels-Alder and Alder Ene Reactions’ Springer Berlin 1984
Fallis AG (1984) Can J Chem 62:183
Ciganek E (1984) Org React 32:1
Fischer K, Hünig S (1987) J Org Chem 52:564
Bovenschulte E, Metz P, Henkel G (1989) Angew Chem Int Ed Engl 28:202
Woo S, Keay BA (1994) Tetrahedron Asymm 5:1411
Mann J (1986) Tetrahedron 42:4611
Reviews on the [4+3] cycloaddition of oxyallyl cations: Rigby JH, Pigge FC to appear in Organic Reactions vol 51
Reviews on the [4+3] cycloaddition of oxyallyl cations: Hosomi A, Tominaga Y (1991) [4+3] Cycloadditions. In: Trost BM, Fleming I (eds) Comprehensive Organic Synthesis, vol 5, Pergamon, Oxford, p 593
Reviews on the [4+3] cycloaddition of oxyallyl cations: Mann J (1986) Tetrahedron 42:4611
Reviews on the [4+3] cycloaddition of oxyallyl cations: Noyori R, Hayakawa Y (1983) Org React 29:163
Reviews on the [4+3] cycloaddition of oxyallyl cations: Harmata M to appear in Lautens M (ed) Advances in Cycloadditions, vol 4, JAI Press and also ref. 128
Hoffmann HMR (1973) Angew Chem Int Ed Engl 12:819
Hoffmann HMR; Clemens KE; Smithers RH (1972) J Am Chem Soc 94:3940
Mann J, Barbosa LCA (1992) J Chem Soc Perkin Trans 1 787
Fukuzawa S, Fukushima M, Fujinami T, Sakai S (1989) Bull Chem Soc Jpn 62:2348
Joshi NN, Hoffmann HMR (1986) Tetrahedron Lett 27:687
Hoffmann HMR, Eggert U, Gibbels U, Giesel K, Koch O, Lies R, Rabe J (1988) Tetrahedron 44:3899
Herter R, Föhlisch B (1982) Synthesis 976
Takaya H, Makino S, Hayakawa Y, Noyori R (1978) J Am Chem Soc 100:1765
Vinter JG, Hoffmann HMR (1973) J Am Chem Soc 95:3051
Murray DH, Albizati KF (1990) Tetrahedron Lett 31:4109
Föhlisch B, Sendelbach S, Bauer H (1987) Liebig Ann Chem 1
Föhlisch B, Krimmer D, Gerlach E, Käshammer D (1988) Chem Ber 121:1585
Föhlisch B, Herter R, Wolf E, Stezowski JJ (1982) Chem Ber 115:355
Sasaki T, Ishibashi Y, Ohno M (1982) Tetrahedron Lett 23:1693
Ohno M, Mori K, Hattori T, Eguchi S (1990) J Org Chem 55:6086
Erden I, Amputch MA (1987) Tetrahedron Lett 28:3779
Noyori R, Nishizawa M, Shimizu F, Hayakawa Y, Maruoka K, Hashimoto S, Yamamoto H, Nozaki H (1979) J Am Chem Soc 101:220
Föhlisch B, Herter R (1984) Chem Ber 117:2580
Harmata M, Gamlath CB (1988) J Org Chem 53:6154
Harmata M, Gamlath CB, Barnes CL (1990) Tetrahedron Lett 31:5981
Harmata M, Fletcher VR, Claassen II RJ (1991) J Am Chem Soc 113:9861
Harmata M, Elahmad S (1993) Tetrahedron Lett 34:789
Harmata M, Jones DE (1996) Tetrahedron Lett 37:783
Harmata M, Elahmad S, Barnes CL (1994) J Org Chem 59:1241
Harmata M, Elomari S, Barnes CL (1996) J Am Chem Soc 118:2860
Schultz AG, Macielag M, Plummer M (1988) J Org Chem 53:391
Lautens M, Aspiotis R, Colucci JT (1996) J Am Chem Soc 118:10930
Henning R, Hoffmann HMR (1982) Tetrahedron Lett 23:2305
Harmata M, Herron BF (1993) J Org Chem 58:7393
Harmata M, Jones DE (1997) J Org Chem 62:1578
Harmata M, Herron BF (1993) Tetrahedron Lett 34:5381
West FG, Chase CE, Arif AM (1993) J Org Chem 58:3794
Davies HML, Clark DM, Smith TK (1985) Tetrahedron Lett 26:5659
Davies HML, Clark DM, Alligood DB, Elband GR (1987) Tetrahedron 43:4265
Davies HML, Ahmed G, Churchill MR (1996) J Am Chem Soc 118:10774
Sammes PG (1986) Gazz Chim Ital 119:109
Katritzky AR, Dennis N (1989) Chem Rev 89:827
Hendrickson JB, Farina JS (1980) J Org Chem 45:3359
Sammes PG, Street LJ (1983) J Chem Soc Perkin Trans 11261
Sammes PG, Street LJ (1982) J Chem Soc Chem Commun 1056
Bromidge SM, Sammes PG, Street LJ (1985) J Chem Soc Perkin Trans I 1725
Sammes PG, Street LJ (1983) J Chem Soc Chem Commun 666
Sammes PG, Street LJ, Whitby RJ (1986) J Chem Soc Perkin Trans 1281
Wender PA, Lee HY, Wilhelm RS, Williams PD (1989) J Am Chem Soc 111:8954
Garst ME, McBride BJ, Douglass III JG (1983) Tetrahedron Lett 24:1675
Williams DR, Benbow JW, Allen EE (1990) Tetrahedron Lett 31:6769
Lupi A, Patamia M, Aramone F (1990) Gazz Chim Ital 120:277
Wender PA, McDonald FE (1990) J Am Chem Soc 112:4956
Wender PA, Mascarenas JL (1991) J Org Chem 56:6267
Feldman KS (1983) Tetrahedron Lett 24:5585
Padwa A, Weingarten MD (1996) Chem Rev 96:223
Ibata T, Jitsuhiro K, Tsubokura Y (1981) Bull Chem Soc Jpn 54:240
Padwa A, Carter SP, Nimmesgern H (1986) J Org Chem 51:1157
Padwa A, Fryxell GE, Zhi L (1988) J Org Chem 53:2875
Padwa A, Fryxell GE, Zhi L (1990) J Am Chem Soc 112:3100
Padwa A, Carter SP, Nimmesgern H, Stull PD (1988) J Am Chem Soc 110:2894
Padwa A, Hornbuckle SF, Fryxell GE, Stull PD (1989) J Org Chem 54:817
McMills MC, Zhuang L, Wright DL, Watt W (1994) Tetrahedron Lett 35:8311
Padwa A, Sandanayaka VP, Curtis EA (1994) J Am Chem Soc 116:2667
Padwa A, Chinn RL, Hornbuckle SF, Zhang ZJ (1991) J Org Chem 56:3271
Pirrung MC, Werner JA (1986) J Am Chem Soc 108:6060
West FG, Eberlein TH, Tester RW (1993) J Chem Soc Perkin Trans 1 2857
Molander GA, Shubert DC (1987) J Am Chem Soc 109:6877
Molander GA, Andrews SW (1989) Tetrahedron Lett 30:2351
Brownbridge P, Chan TH (1979) Tetrahedron Lett 4437
Lee SD, Chan TH (1984) Tetrahedron 40:3611
Molander GA, Cameron KO (1991) J Org Chem 56:2617
Molander GA, Cameron KO (1993) J Am Chem Soc 115:830
Molander GA, Cameron KO (1993) J Org Chem 58:5931
Molander GA, Eastwood PR (1995) J Org Chem 60:8382
Molander GA, Siedem CS (1995) J Org Chem 60:130
Kobayashi K, Sasaki A, Kanno Y, Suginome H (1991) Tetrahedron 47:7245
Molander GA, McKie JA (1993) J Org Chem 58:7216
Harmata M, Murray T (1989) J Org Chem 54:3761
Davies SG, Polywka MEC, Thomas SE (1986) J Chem Soc Perkin Trans I 1277
Alvarez E, Diaz MT, Rodriguez ML, Martin JD (1990) Tetrahedron Lett 31:1629
Zarraga M, Martin JD (1991) Tetrahedron Lett 32:2249
Alvarez E, Zurita D, Martin JD (1991) Tetrahedron Lett 32:2245
Rigby JH, Zbur Wilson JA (1987) J Org Chem 52:34
Gebel RC, Margaretha P (1992) Helv Chim Acta 75:1633
Fattori D, Vogel P (1993) Tetrahedron Lett 34:1017
Schmidt RR, Beitzke C, Forrest AK (1982) J Chem Soc Chem Commun 909
Le Drian C, Vieira E, Vogel P (1989) Helv Chim Acta 72:338
Le Drian C, Vogel P (1987) Helv Chim Acta 70:1703
Auberson Y, Vogel P (1989) Helv Chim Acta 72:278
Nativi C, Reymond JL, Vogel P (1989) Helv Chim Acta 72:882
Warm A, Vogel P (1986) J Org Chem 51:5348
Takahashi T, Iyobe A, Arai Y, Koizumi T (1989) Synthesis 189
Brown HC, Vara Prasad JVN (1985) J Org Chem 50:3002
Rama Rao AV, Yadav JS, Vidyasagar V (1985) J Chem Soc Chem Commun 55
Arjona O, Fernandez de la Pradilla R, Perez RA, Plumet J (1988) Tetrahedron 44:7199
La BeUe BE, Knudsen MJ, Olmstead MM, Hope H, Yanuch MD, Schore NE (1985) J Org Chem 50:5215
Sampath V, Schore NE (1985) J Org Chem 48:4882
Fattori D, de Guchteneere E, Vogel P (1989) Tetrahedron Lett 30:7415
Black KA, Vogel P (1986) J Org Chem 51:5341
Reymond JL, Vogel P (1989) Tetrahedron Lett 30:705
Reymond JL, Pinkerton AA, Vogel P (1991) J Org Chem 56:2128
Arjona O, Fernandez de la Pradilla R, Garcia L, Mallo A, Plumet J (1989) J Chem Soc Perkin Trans II1315
Arjona O, Fernandez de la Pradilla F, Garcia E, Martin-Domenech A, Plumet J (1989) Tetrahedron Lett 30:6437
Arjona O, Fernandez de la Pradilla R, Martin-Domenech A, Plumet J (1990) Tetrahedron 46:8187
Arjona O, Fernandez de la Pradilla R, Mallo A, Perez S, Plumet J (1989) J Org Chem 54:4158
Arjona O, Fernandez de la Pradilla R, Manzano C, Perez S, Plumet J Tetrahedron Lett (1987) 28:5547
Arjona O, Fernandez de la Pradilla R, Perez S, Plumet J (1988) Tetrahedron 44:1235
Moursounidis J, Wege D (1983) Aust J Chem 36:2473
Gasparini F Vogel P (1989) Helv Chim Acta 72:271
Bialecki M, Vogel P (1994) Tetrahedron Lett 35:5213
Bialecki M, Vogel P (1995) Helv Chim Acta 78:325
Ager DJ, East MB (1994) Heterocycles 37:1789
Katagiri N, Akatsuka H, Kaneko C, Sera A (1988) Tetrahedron Lett 29:5397
Katagiri N, Akatsuka H, Haneda T, Kaneko C (1987) Chem Lett 2257
Lautens M, Abd-El-Aziz AS, Lough AJ (1990) J Org Chem 55:5305
Lautens M, Ma S, Yee A (1995) Tetrahedron Lett 36:4185
White JD, Fukuyama Y (1979) J Am Chem Soc 101:226
Kim H, Ziani-Cherif C, Oh J, Cha JK (1995) J Org Chem 60:792
Lautens M, Belter RK (1992) Tetrahedron Lett 33:2617
Arjona O, de Dios A, Fernandez de la Pradilla R, Plumet J, Viso A (1994) J Org Chem 59:3906
Sammes PG, Street LJ (1983) J Chem Soc Perkin Trans I 2729
Williams DR, Benbow JW, McNutt JG, Allen EE (1995) J Org Chem 60:833
Ager DJ, East MB (1993) Tetrahedron 49:5683
Lautens M, Ma S (1996) Tetrahedron Lett 37:1727
Uozumi Y, Hayashi T (1993) Tetrahedron Lett 34:2335
Bunn BJ, Cox PJ, Simpkins NS (1993) Tetrahedron 49:207
Simpkins NS (1996) Pure & Appl Chem 68:691
Sweger RW, Czarnik AW (1991) Retrograde Diels-Alder Reactions in Trost BM, Fleming I (eds) Comprehensive Organic Synthesis, vol 5, Pergamon, Oxford, p 551
Lautens M (1993) Synlett 177
Lautens M (1993) Pure & Appl Chem 64:1873
Lautens M, Ren Y, Delanghe PHM, Chiu P, Ma S, Colucci J (1995) Can J Chem 73:1251
Keay BA, Woo S (1996) Synthesis 669
Arvai G, Fattori D, Vogel P (1992) Tetrahedron 48:10621
Roser K, Carrupt PA, Vogel P, Honegger E, Heilbronner E (1990) Helv Chim Acta 73:1
de Guchteneere E, Fattori D, Vogel P (1992) Tetrahedron 48:10603
Noyori R, Sato T, Hyakawa Y (1978) J Am Chem Soc 100:2561
Arco MJ, Trammell MH, White JD (1976) J Org Chem 41:2075
Hoffmann HMR (1984) Angew Chem Int Ed Engl 23:1
Sato T, Hayakawa Y, Noyori R (1984) Bull Chem Soc Jpn 57:2515
Auberson Y, Vogel P (1989) Angew Chem Int Ed Engl 28:1498
Bimwala RM, Vogel P (1992) J Org Chem 57:2076
Sevin AF, Vogel P (1994) J Org Chem 59:5920
Cowling AP, Mann J, Usmani AA (1981) J Chem Soc Perkin Trans I 2116
Bimwala M, Vogel P (1989) Helv Chim Acta 72:1825
Alvarez E, Diaz MT, Perez R, Martin JD (1991) Tetrahedron Lett 32:2241
Shizuri Y, Nishiyama S, Shigemori H, Yamamura S (1985) J Chem Soc Chem Commun 292
Klein LL (1985) J Am Chem Soc 107:2573
Meinwald J (1977) Pure & Appl Chem 49:1275
Just G, Liak TJ, Lim M-I, Potvin P, Tsantrizos YS (1980) Can J Chem 58:2024
Murai A, Takahashi K, Taketsuru H, Masamune T (1981) J Chem Soc Chem Commun 221
Ohno M, Ito Y, Arita F, Shibata T, Adachi K, Sawai H (1984) Tetrahedron 40:145
Shimizu M, Matsukawa K, Fujisawa T (1993) Bull Soc Chem Jpn 66:2128
Matsuki K, Inoue H, Takeda M (1993) Tetrahedron Lett 34:1167
Jones JB, Francis CJ (1984) Can J Chem 62:2578
Bloch R, Gibe-Jampel E, Girard C (1985) Tetrahedron Lett 26:4087
Das J, Hanslanger MF, Gougoutas JZ, Malley MF (1987) Synthesis 1100
Seebach D, Jaeschke G, Wang YM (1995) Angew Chem Int Ed Engl 34:2395
Kozikowski AP, Ames A (1981) J Am Chem Soc 103:3923
Schlessinger RH, Pettus TRR (1994) J Org Chem 59:3246
Katagiri N, Akatsuka H, Haneda T, Kaneko C (1988) J Org Chem 53:5464
Padwa A, Zhi L, Fryxell GE (1991) J Org Chem 56:1077
Imagawa T, Sugita S, Akiyama T, Kawanisi M (1981) Tetrahedron Lett 22:2569
Akiyama T, Fujii T, Ishiwari H, Imagawa T, Kawanisi M (1978) Tetrahedron Lett 2165
Imagawa T, Nurai H, Akiyama T, Kawanisi M (1979) Tetrahedron Lett 1691
Imagawa T, Sonobe T, Ishiwari H, Akiyama T, Kawanisi M (1980) J Org Chem 45:2005
Harmata M, Gamlath CB, Barnes CL (1990) Tetrahedron Lett 31:5981
Harmata M, Gamlath CB, Barnes CL (1995) J Org Chem 60:5077
Wang WB, Roskamp EJ (1992) Tetrahedron Lett 33:7631
Gravel D, Deziel R, Brisse F, Hechler L (1981) Can J Chem 59:2997
Garver LC, van Tamelen EE (1982) J Am Chem Soc 104:867
Van RoyenLA, Mijngheer R, De Clerq PJ (1983) Tetrahedron Lett 24:3145
Rajapaksa D, Keay BA, Rodrigo R (1984) Can J Chem 62:826
Campbell MM, Kaye AD, Sainsbury M (1983) Tetrahedron Lett 24:4745
Campbell MM, Kaye AD, Sainsbury M, Yavarzedeh R (1984) Tetrahedron 40:2461
Brion F (1982) Tetrahedron Lett 5299
Koreeda M, Jung KY, Ichita J (1989) J Chem Soc Perkin Trans I 2129
Leroy J, Fischer N, Wakselman C (1990) J Chem Soc Perkin Trans I 1281
Grootaert WM, De Clerq PJ (1986) Tetrahedron Lett 27:1731
Takahashi T, Kotsubo H, Iyobe A, Namiki T, Koizumi T (1990) J Chem Soc Perkin Trans I 3065
Kinder Jr FR, Bair KW (1994) J Org Chem 59:6965
Yang W, Koreeda M (1992) J Org Chem 57:3836
Guildford A, Turner RW (1983) J Chem Soc Chem Commun 466
Acena JL, Arjona O, Fernandez de la Pradilla R, Plumet J, Viso A (1992) J Org Chem 57:1945
Metz P, Cramer E (1993) Tetrahedron Lett 34:6371
Metz P, Stölting J, Läge M, Krebs B (1994) Angew Chem Int Ed Engl 33:2195
Molander GA, Eastwood PR (1995) J Org Chem 60:4559
Arjona O, de Dios A, Fernandez de la Pradilla R, Plumet J (1991) Tetrahedron Lett 32:7309
Le Drian C, Vionnet JP, Vogel P (1990) Helv Chim Acta 73:161
Arjona O, Conde S, Plumet J, Viso A (1995) Tetrahedron Lett 34:6157
Bhatt MV, Kulkarni SU (1983) Synthesis 249
Eggelte TA, de Koning H, Huisman HO (1979) Rec Trav Chim Pays-Bas 98:267
Antonsson T, Vogel P (1990) Tetrahedron Lett 31:89
Wong HNC, Ng TK, Wong TY, Xing YD (1984) Heterocydes 22:875
Lajunen M, Kaitaranta E, Dahlqvist M (1994) Acta Chem Scand 48:399
Lajunen M, Uotila R (1992) Acta Chem Scand 46:968
Lajunen M, Maki E (1991) Acta Chem Scand 45:578
Yates PY, Douglas SP (1982) Can J Chem 60:2760
Ogawa S, Iwasawa Y, Taisuke N, Suami T, Ohba S, Ito M, Saito Y (1985) J Chem Soc Perkin Trans I 903
Ogawa S, Tsunoda H (1992) Liebigs Ann Chem 637
Smith AB, Liverton NJ, Hrib, NJ, Sivaramakrishnan H, Winzenberg K (1985) J Org Chem 50:3239
Smith AB, Liverton NJ, Hrib NJ, Sivaramakrishnan H, Winzenberg K (1986) J Am Chem Soc 108:3040
Best WM, Wege D (1981) Tetrahedron Lett 22:4877
Giles RGF, Hughes AB, Sargent MV (1991) J Chem Soc Perkin Trans 1 1581
Batt DG, Jones DG, La Greca S (1991) J Org Chem 56:6704
Takaya H, Hayakawa Y, Makino S, Noyori R (1978) J Am Chem Soc 100:1778
Kato T, Suzuki T, Ototani N, Maeda H, Yamada K, Kitahara Y (1977) J Chem Soc Perkin Trans I 206
Kitahara Y, Kato T, Ototani N, Inoue A, Izumi H (1968) J Chem Soc (C) 2508
Borthwick AD, Curry DJ, Poynton A, Whalley WB, Hooper JW (1980) J Chem Soc Perkin Trans I 2435
Koreeda M, Gopalaswamy R (1995) J Am Chem Soc 117:10595
Montana AM, Nicholas KM, Khan MA (1988) J Org Chem 53:5193
Montana AM, Nicholas KM (1990) J Org Chem 55:1569
Cummins WJ, Drew MGB, Mann J, Markson AJ (1988) Tetrahedron 44:5151
de Almeida Barbosa L-C, Mann J (1990) J Chem Soc Perkin Trans I 177
Dienes Z, Antonsson T, Vogel P (1993) Tetrahedron Lett 34:1013
Barbosa LCA, Mann J, Wilde PD (1989) Tetrahedron 45:4619
Stohrer I, Hoffmann HMR (1992) Tetrahedron 48:6021
Ashworth RW, Berchtold GA (1977) Tetrahedron Lett 339
Hogeveen H, Middelkoop TB (1973) Tetrahedron Lett 3671
Grieco PA, Zelle RE, Lis R, Finn J (1983) J Am Chem Soc 105:1403
Grieco PA, Lis R, Zelle RE, Finn J (1986) J Am Chem Soc 108:5908
Forsey SP, Rajapaksa D, Taylor NJ, Rodrigo R (1989) J Org Chem 54:4280
Pelter A, Ward RS, Li Q, Pis J (1994) Tetrahedron Asymm 5:909
De Geyter T, Cauwberghs S, De Clercq (1994) Bull Soc Chim Belg 103:433
Cauwberghs SG, De Clercq PJ (1988) Tetrahedron Lett 29:6501
De Schrijver J, De Clerq PJ (1993) Tetrahedron Lett 34:4369
Cossy J, Ranaivosata JL, Bellosta V, Ancerewicz J, Ferritto R, Vogel P (1995) J Org Chem 60:8351
Jung ME, Street LJ (1984) J Am Chem Soc 106:8327
Wender PA, Kogen H, Lee HY, Munger Jr JD, Wilhelm RS, Williams PD (1989) J Am Chem Soc 111:8957
Yadav JS, Ravishankar R, Lakshman S (1994) Tetrahedron Lett 35:3617
Yadav JS, Ravishankar R, Lakshman S (1994) Tetrahedron Lett 35:3621
Lautens M, Chiu P (1991) Tetrahedron Lett 32:4827
Lautens M, Smith AC, Abd-El-Aziz A, Huboux AH (1990) Tetrahedron Lett 31:3253
Krishnamurthy S, Brown HC (1979) J Org Chem 44:3678
Moss RJ, Rickborn B (1985) J Org Chem 50:1381
Lautens M, Chiu P, Colucci JT (1993) Angew Chem Int Ed Engl 32:281
Woo S, Keay BA (1992) Tetrahedron Lett 33:2661
Lautens M, Chiu P, Ma S, Rovis T (1995) J Am Chem Soc 117:532
The reaction conditions have been optimized (<2mol% catalyst), T. Rovis, U. Toronto, submitted for publication
Lautens M, Ma S (1997) J Am Chem Soc 119:0000
Lautens M, Klute W (1996) Angew Chem Int Ed Engl 35:442
Lautens M, Kumanovic S, Meyer C (1996) Angew Chem Int Ed Engl 35:1329
Cossy J, Aclinou P, Bellosta V, Furet N, Baranne-Lafont J, Sparfel D, Souchaud C (1991) Tetrahedron Lett 32:1315
Caple R, Chen GMS, Nelson JD (1971) J Org Chem 36:2874
Jeffrey AM, Yeh HJC, Jerina DM, DeMarinis RM, Foster CH, Piccolo DE, Berchtold GA (1974) J Am Chem Soc 96:6929
Arjona O, de Dios A, Plumet J (1993) Tetrahedron Lett 34:7451
Arjona O, Fernandez de la Pradilla R, Mallo A, Plumet J, Viso A (1990) Tetrahedron Lett 31:1475
Acena JL, Arjona O, Iradier F, Plumet J (1996) Tetrahedron Lett 37:105
Lautens M, Chiu P (1993) Tetrahedron Lett 34:773.
Lautens M, Fillion E (1996) J Org Chem 61:7994 and references to earlier examples of the “pincer” Diels-Alder reaction
Metz P, Meiners U, Fröhlich R, Grehl M (1994) J Org Chem 59:3687
Metz P, Meiners U, Cramer E, Fröhlich R, Wibbeling B (1996) Chem Commun 431
Lautens M, Ma S, Belter RK, Chiu P, Leschziner A (1992) J Org Chem 57:4065
Lautens M, Gajda C (1993) Tetrahedron Lett 34:4591
Lautens M, Kumanovic S (1995) J Am Chem Soc 117:1954
Lautens M, Gajda C, Chiu P (1993) J Chem Soc Chem Commun 1193
Lautens M, Di Felice C, Huboux A (1989) Tetrahedron Lett 30:6817
Lautens M, Belter RK, Lough AJ (1992) J Org Chem 57:422
Duan JP, Cheng CH (1993) Tetrahedron Lett 34:4019
Moinet C, Fiaud JC (1995) Tetrahedron Lett 36:2051
Lautens M, Ma S (1996) J Org Chem 61:7246
Author information
Authors and Affiliations
Editor information
Rights and permissions
Copyright information
© 1997 Springer Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Chiu, P., Lautens, M. (1997). Using ring-opening reactions of oxabicyclic compounds as a strategy in organic synthesis. In: Metz, P. (eds) Stereoselective Heterocyclic Synthesis II. Topics in Current Chemistry, vol 190. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119245
Download citation
DOI: https://doi.org/10.1007/BFb0119245
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-62700-5
Online ISBN: 978-3-540-68447-3
eBook Packages: Springer Book Archive