Abstract
The term Lewis acid catalysts generally refers to metal salts like aluminium chloride, titanium chloride and zinc chloride. Their application in asymmetric catalysis can be achieved by the addition of enantiopure ligands to these salts. However, not only metal centers can function as Lewis acids. Compounds containing carbenium, silyl or phosphonium cations display Lewis acid catalytic activity. In addition, hypervalent compounds based on phosphorus and silicon, inherit Lewis acidity. Furthermore, ionic liquids, organic salts with a melting point below 100 °C, have revealed the ability to catalyze a range of reactions either in substoichiometric amount or, if used as the reaction medium, in stoichiometric or even larger quantities. The ionic liquids can often be efficiently recovered. The catalytic activity of the ionic liquid is explained by the Lewis acidic nature of their cations. This review covers the survey of known classes of metal-free Lewis acids and their application in catalysis.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Noyori R (1994) Asymmetric catalysis in organic synthesis. Wiley, New York
Jacobsen EN, Pfaltz A, Yamamoto H (1999) Comprehensive asymmetric catalysis. Springer, Berlin Heidelberg New York
Schinzer D (1989) Selectivities in Lewis acid promoted reactions. Kluwer Academic, Dordrecht
Pierre J-L (2000) Chem Soc Rev 29:251
Roberts BP (1999) Chem Soc Rev 28:25
Jensen WB (1980) The Lewis acid-base concept. Wiley, New York
Jensen WB (1978) Chem Rev 78:1
Ma D, Cheng K (1999) Tetrahedron Asymmetry 10:713
Schuster T, Bauch M, Dürner G, Göbel MW (2000) Org Lett 2:179
O’Donnell MJ (1993) In: Ojima I (ed) Catalytic asymmetric synthesis. Verlag Chemie, New York
Shioiri T (1997) In: Sasson Y, Neumann R (eds) Handbook of phase-transfer cataylsis. Blackic Academic and Professional, London
O’Donnell MJ (1998) Phases Sachem Phase-Transfer Catal Rev 4:5
O’Donnell MJ (1999) Phases Sachem Phase-Transfer Catal Rev 5:5
Shioiri T, Arai S (2000) In: Vogtle F, Stoddart JF, Shibasaki M (eds) Stimulating concepts in chemistry. Wiley-VCH, Weinheim
O’Donnel MJ (2001) Aldrichim Acta 34:3
Maruoka K, Ooi T (2003) Chem Rev 103:3013
O’Donnell MJ (2004) Acc Chem Res 37:506
Lygo B, Andrews BI (2004) Acc Chem Res 37:518
Ooi T, Maruoka K (2004) Acc Chem Res 37:526
Corey EJ (2002) Angew Chem Int Ed 41:1650
Ishihara K (2000) In: Yamamoto H (ed) Lewis acids in organic synthesis, vol 1. Wiley-VCH, Weinheim p 135
James TD, Shinkai S (2002) Top Curr Chem 218:159
Yamamoto H, Futatsugi K (2005) Angew Chem Int Ed 44:1924
Dilman AD, Ioffe SL (2003) Chem Rev 103:733
Olah GA, Rasul G, Prakash GKS (1999) J Am Chem Soc 121:9615
Olah GA, Rasul G, Prakash GKS (1996) J Organomet Chem 521:271
Mathieu B, deFays L, Ghosez L (2000) Tetrahedron Lett 41:9561
Jonas S, Simchen G (1998) J Prakt Chem 340:506
Mathieu B, Ghosez L (1997) Tetrahedron Lett 38:5497
Johannsen M, Jorgenson KA, Helmchen G (1998) J Am Chem Soc 120:7637
Maigrot N, Mazaleyrat JP, Welvart Z (1985) J Org Chem 50:3916
Mazaleyrat J-P, Wakselman M (1996) J Org Chem 61:2695
Adams R, Binder LO (1941) J Am Chem Soc 63:2773
Corey JY (1975) J Am Chem Soc 97:3237
Corey JY, West R (1963) J Am Chem Soc 85:2430
Tang Z, Mathieu B, Tinant B, Dive G, Ghosez L (2007) Tetrahedron 63:8449
Hara K, Akiyama R, Sawamura M (2005) Org Lett 7:5621
Lambert JB, Zhang S (1993) Chem Commun 383
Orito Y, Nakajima M (2006) Synthesis 1391
Denmark SE, Fu J (2003) Chem Commun 167
Rendler S, Oestreich M (2005) Synthesis 1727
Holmes RR (1996) Chem Rev 96:927
Chuit C, Corriu RJP, Reye C, Young JC (1993) Chem Rev 93:1371
Dalko PI, Moisan L (2004) Angew Chem Int Ed 43:5138
Denmark SE, Coe DM, Pratt NE, Griedel BD (1994) J Org Chem 59:6161
Angell RM, Barret AGM, Braddock DC, Swallow S, Vickery BD (1997) Chem Commun 919
Iseki K, Kuroki Y, Takahashi M, Kobayashi Y (1996) Tetrahedron Lett 37:5149
Iseki K, Kuroki Y, Takahashi M, Kishimoto S, Kobayashi Y (1997) Tetrahedron 53:3513
Malkov AV, Bell M, Vassieu M, Bugatti V, Kocovsky P (2002) Org Lett 4:1047
Malkov AV, Bell M, Vassieu M, Bugatti V, Kocovsky P (2003) J Mol Catal A Chem 196:179
Malkov AV, Dufková L, Farrugia L, Kocovský P (2003) Angew Chem Int Ed 42:3674
52. Malkov AV, Bell M, Orsini M, Pernazza D, Massa A, Herrmann P, Meghani P, Kocovsky P (2003) J Org Chem 68:9659
53. Shimada T, Kina A, Ikeda S, Hayashi T (2002) Org Lett 4:2799
54. Shimida T, Kina A, Hayashi T (2003) J Org Chem 68:6329
55. Kina A, Shimada T, Hayashi T (2004) Adv Synth Catal 346:1169
56. Traverse JF, Zhao Y, Hoveyda AH, Snapper ML (2005) Org Lett 7:3151
Iseki K, Mizuno S, Kuroki Y, Kobayashi Y (1998) Tetrahedron Lett 39:2767
Iseki K, Mizuno S, Kuroki Y, Kobayashi Y (1999) Tetrahedron 55:977
Gilman H, Atwell WH (1964) J Am Chem Soc 86:2687
Kinnaird JWA, Ng PY, Kubota K, Wang X, Leighton JL (2002) J Am Chem Soc 124:7920
Denmark SE, Jacobs RT, Dai-Ho G, Wilson S (1990) Organometallics 9:3015
Myers AG, Kephart SE, Chen H (1992) J Am Chem Soc 114:7922
Denmark SE, Griedel BD, Coe DM (1993) J Org Chem 58:988
Denmark SE, Griedel BD, Coe DM, Schnute ME (1994) J Am Chem Soc 116:7026
Matsumoto K, Oshima K, Utimoto K (1994) J Org Chem 59:7152
Zhang X, Houk KN, Leighton JL (2005) Angew Chem Int Ed 44:938
Kubota K, Leighton JL (2003) Angew Chem Int Ed 42:946
Hackman BM, Lombardi PJ, Leighton JL (2004) Org Lett 6:4375
Berger R, Rabbat MA, Leighton JL (2003) J Am Chem Soc 125:9596
Berger R, Duff K, Leighton JL (2004) J Am Chem Soc 126:5686
Ogawa C, Konishi H, Sugiura M, Kobayashi S (2004) Org Biomol Chem 2:446
Ogawa C, Sugiura M, Kobayashi S (2004) Angew Chem Int Ed 43:6491
Breslin HJ, Cai C, Miskowski TA, Coutinho SV, Zhang S-P, Hornby P, He W (2006) Bioorg Med Chem Lett 16:2505
Balboni G, Onnis V, Congiu C, Zotti M, Sasaki Y, Ambo A, Bryant SD, Jinsmaa Y, Lazarus LH, Trapella C, Salvadori S (2006) J Med Chem 49:5610
Perl NR, James JL (2007) Org Lett 9:3699
Kobayashi S, Ogawa C, Konishi H, Sugiura M (2003) J Am Chem Soc 125:6610
Massa A, Malkov AV, Kocovsky P, Scettri A (2003) Tetrahedron Lett 44:7179
Massa A, Malkov AV, Kocovsky P, Scettri A (2003) Tetrahedron Lett 44:9067
Rowlands GJ, Barnes WK (2003) Chem Commun, 2712
Denmark SE, Winter SBD, Su X, Wong K-T (1996) J Am Chem Soc 118:7404
Denmark SE, Wong K-T, Stavenger RA (1997) J Am Chem Soc 119:2333
Denmark SE, Stavenger RA, Wong K-T (1998) J Org Chem 63:918
Denmark SE, Stavenger RA, Su X, Wong K-T, Nishigaichi Y (1998) Pure Appl Chem 70:1469
Denmark SE, Stavenger RA, Wong K-T (1998) Tetrahedron 54:10389
Denmark SE, Stavenger RA (1998) J Org Chem 63:9524
Denmark SE, Su X, Nishigaichi Y (1998) J Am Chem Soc 120:12990
Denmark SE, Stavenger RA, Wong K-T, Su X (1999) J Am Chem Soc 121:4982
Denmark SE, Pham SM (2000) Helv Chim Acta 83:1846
Denmark SE, Stavenger RA (2000) J Am Chem Soc 122:8837
Denmark SE, Pham SM (2003) J Org Chem 68:5045
Denmark SE, Stavenger RA (2000) Acc Chem Res 33:432
Denmark SE, Wynn T (2001) J Am Chem Soc 123:6199
Denmark SE, Wynn T, Beutner GL (2002) J Am Chem Soc 124:13405
Denmark SE, Heemstra JR (2003) Org Lett 5:2303
Denmark SE, Beutner GL, Wynn T, Eastgate MD (2005) J Am Chem Soc 127:3774
Denmark SE, Beutner GL (2003) J Am Chem Soc 125:7800
Denmark SE, Heemstra JR (2004) Synlett, 2411
Denmark SE, Fan Y (2003) J Am Chem Soc 125:7825
Denmark SE, Fan Y (2002) J Am Chem Soc 124:4233
Nakajima M, Yokota T, Saito M, Hashimoto S (2004) Tetrahedron Lett 45:61
Iwasaki F, Onomura O, Mishima K, Maki T, Matsumura Y (1999) Tetrahedron Lett 40:7507
Iwasaki F, Onomura O, Mishima K, Kanematsu T, Maki T, Matsumura Y (2001) Tetrahedron Lett 42:2525
Malkov AV, Mariani A, MacDougall KN, Kocovsky P (2004) Org Lett 6:2253
Denmark SE, Barsanti PA, Wong K-T, Stavenger RA (1998) J Org Chem 63:2428
Nakajima M, Saito M, Uemura M, Hashimoto S (2002) Tetrahedron Lett 43:8827
Tokuoka E, Kotani S, Matsunaga H, Ishizuka T, Hashimoto S, Nakajima M (2005) Tetrahedron Asymmetry 16:2391
Shirakawa S, Berger R, Leighton JL (2005) J Am Chem Soc 127:2858
Shirakawa S, Lombardi PJ, Leighton JL (2005) J Am Chem Soc 127:9974
Kubota K, Hamblett CL, Wang X, Leighton JL (2006) Tetrahedron 62:11397
Rao JS, Briere J-F, Metzer P, Basavaiah D (2006) Tetrahedron Lett 47:3553
Myers EL, deVries JG, Aggarwal VK (2007) Angew Chem Int Ed 46:1893
Terada M, Kouchi M (2006) Tetrahedron 62:401
Akiba K-Y (1999) Wiley-VCH, Weinheim
Sinnott M (1988) Adv Phys Org Chem 24:113
Kluger R, Tayler SD (1990) J Am Chem Soc 112:6669
Mukaiyama T, Matsui S, Kashiwagi K (1989) Chem Lett 993
Mukaiyama T, Kashiwagi K, Matsui S (1989) Chem Lett 1397
Cordoba R, Plumet J (2003) Tetrahedron Lett 44:6157
Wang X, Tain S-K (2007) Tetrahedron Lett 48:6010
Amurrio I, Córdoba R, Csáky AG, Plumet J (2004) Tetrahedron 60:10521
Kurono N, Yamaguchi M, Suzuki K, Ohkuma T (2005) J Org Chem 70:6530
Johnson CL, Donkor RE, Nawaz W, Karodia N (2004) Tetrahedron Lett 45:7359
Selva M, Perosa A, Tundo P, Brunelli D (2006) J Org Chem 71:5770
Hon Y-S, Lee C-F (2001) Tetrahedron 57:6181
Hon Y-S, Lee C-F (1999) Tetrahedron Lett 40:2389
Hon Y-S, Lee C-F, Chen R-J, Szu P-H (2001) Tetrahedron 57:5991
Speziale AJ, Ratts KW (1963) J Am Chem Soc 85:2790
Fliszar S, Hudson RF, Salvadori G (1963) Helv Chim Acta 46:1580
Bordwell FG (1988) Acc Chem Res 21:456
Issleib K, Linder R (1967) Liebigs Ann Chem 707:120
Olah AG, Prakash GKS, Liang G (1977) 42:2666
Olah AG (2001) J Org Chem 66:5943
Shchepinov MS, Korshun VA (2003) Chem Soc Rev 32:170
Mukaiyama T, Kobayashi S, Shoda S (1984) Chem Lett 907
Mukaiyama T, Kobayashi S, Shoda S (1984) Chem Lett 1529
Mukaiyama T, Kobayashi S, Murakami M (1984) Chem Lett 1759
Mukaiyama T, Kobayashi S, Murakami M (1985) Chem Lett 447
Kobayashi S, Murakami M, Mukaiyama T (1985) Chem Lett 953
Ohshima M, Murakami M, Mukaiyama T (1985) Chem Lett 1871
Mukaiyama T, Kobayashi S, Tamura M, Sagawa Y (1987) Chem Lett 491
Kobayashi S, Matsui S, Mukaiyama T (1988) Chem Lett 1491
Mukaiyama T, Akamatsu H, Han JS (1990) Chem Lett 889
Holli TK, Bosnich B (1995) J Am Chem Soc 117:4570
Denmark SE, Chen C-T (1994) Tetrahedron Lett 35:4327
Chen C-T, Chao S-D, Yen K-C (1998) Synlett 924
Olah GA, Liang G (1975) J Org Chem 40:2108
Chen C-T, Chao S-D, Yen K-C, Chen CH, Chou I-C, Hon S-W (1997) J Am Chem Soc 119:11341
Chen C-T, Chao S-D (1999) J Org Chem 64:1090
Armarego WLF, Sharma SC (1970) J Chem Soc (C):1600
Mukaiyama T, Yanagisawa M, Iida D, Hachiya I (2000) Chem Lett 606
Yanagisawa M, Shimamura T, Iida D, Matsuo J-I, Mukaiyama T (2000) Chem Pharm Bull 48:1838
Yanagisawa M, Mukaiyama T (2001) Chem Lett:224
Riant O, Samuel O, Kagan HB (1993) J Am Chem Soc 115:5835
Taudien S, Riant O, Kagan HB (1995) Tetrahedron Lett 36:3513
Brunner A, Taudien S, Riant O, Kagan HB (1997) Chirality 9:478
Sammakia T, Latham H (1995) Tetrahedron Lett 36:6867
Connelly NG, Geiger WE (1996) Chem Rev 96:877
Magdziak D, Pettus LH, Pettus RR (2001) Org Lett 3:557
Bjurling E, Berg U, Andersson C-M (2002) Organometallics 21:1583
Nicolas C, Herse C, Lacour J (2005) Tetrahedron Lett 46:4605
Laursen BW, Krebs FC (2000) Angew Chem Int Ed 39:3432
Laursen BW, Krebs FC (2001) Chem Eur J 7:1773
Nicolas C, Lacour J (2006) Org Lett 8:4343
Wasserscheid P, Welton T (2003) Ionic liquids in synthesis. Wiley-VCH, Weinheim
Rogers RD, Seddon KR (2003) ACS Symposium Series 856. American Chemical Society, Washington DC, p 2
Katritzky AR, Singh S, Kirichenko K, Holbrey JD, Smiglak M, Reichert WM, Rogers RD (2005) Chem Commun 868
Fukumoto K, Yoshizawa M, Ohno H (2005) J Am Chem Soc 127:2398
Carter EB, Culver SL, Fox PA, Goode RD, Ntai I, Tickell MD, Traylor RK, Hoffman NW, Davis JH (2004) Chem Commun 630
Imperato G, Eibler E, Niedermaier J, König B (2005) Chem Commun 1170
Welton T (1999) Chem Rev 99:2071
Zhao D, Wu M, Kou Y, Min E (2002) Catal Today 74:157
Baudequin C, Baudoux J, Levillain J, Cahard D, Gaumont AC, Plaquevent JC (2003) Tetrahedron Asymmetry 14:3081
Jain N, Kumar A, Chauhan S, Chauhan SMS (2005) Tetrahedron 61:1015
Parvulescu VI, Hardacre C (2007) Chem Rev 107:2615
Ding J, Armstrong DW (2005) Chirality 17:281
Baudequin C, Bregeon D, Levillain J, Guillen F, Plaquevent JC, Gaumont AC (2005) Tetrahedron Asymmetry 16:3921
Winkel A, Reddy PVG, Wilhelm R (2008) Synthesis 999
Malhotra SV, Wang Y (2006) Tetrahedron: Asymmetry 17:1032
Luo S, Mi X, Zhang L, Liu S, Xu H, Cheng J-P (2006) Angew Chem Int Ed 45:3093
Howarth J, Hanlon K, Fayne D, McCormac P (1997) Tetrahedron Lett 38:3097
Harlow KJ, Hill AF, Welton T (1996) Synthesis 697
Fischer T, Sethi A, Welton T, Woolf J (1999) Tetrahedron Lett 40:793
Earle MJ, McCormac PB, Seddon KR (1999) Green Chem 1:23
Xiao Y, Malthotra SV (2004) Tetrahedron Lett 45:8339
Tao G-H, He L, Liu W-S, Xu L, Xiong W, Wang T, Kou Y (2006) Green Chem 8:639
Bica K, Gmeiner G, Reichelt C, Lendl B, Gaertner P (2007) Synthesis 1333
Aggarwal A, Lancaster NL, Sethi AR, Welton T (2002) Green Chem 4:517
Vidiš A, Ohlin CA, Laurenczy G, Küsters E, Sedelmeier G, Dyson PJ (2005) Adv Synth Catal 347:266
Tsuzuki S, Tokuda H, Mikami M (2007) Phys Chem Chem Phys 9:4780
Yadav JS, Reddy BVS, Reddy JSS, Rao RS (2003) Tetrahedron 59:1599
Jurčík V, Wilhelm R (2006) Tetrahedron Asymmetry 17:801
Jurcík V, Wilhelm R (2004) Tetrahedron 60:3205
Jurčík V, Wilhelm R (2005) Org Biomol Chem 3:239
Wang Z, Wang Q, Zhang Y, Bao W (2005) Tetrahedron Lett 46:4657
Ou W-H, Huang Z-Z (2006) Green Chem 8:731
Yadav JS, Reddy BVS, Raj KS, Prasad AR (2003) Tetrahedron 59:1805
Peng J, Deng Y (2001) Tetrahedron Lett 42:5917
Xu L-W, Li J-W, Zhou S-L, Xia C-G (2004) New J Chem 28:183
Yadav JS, Reddy BVS, Baishya G (2003) J Org Chem 68:7098
Brindaban CR, Subhash B, Das A (2006) Tetrahedron Lett 47:881
Wang Y-N, Ni B, Headley AD, Li G (2007) Adv Synth Catal 349:319
Shen Z-L, Ji S-J, Loh T-P (2005) Tetrahedron Lett 46:3137
Blanrue A, Wilhelm R (2004) Synlett 2621
Jurčík V, Wilhelm R (2005) Green Chem 7:844
Aggarwal VK, Emme I, Mereeu A (2002) Chem Commun 1612
Hsu J-C, Yen Y-H, Chu Y-H (2004) Tetrahedron Lett 45:4673
Pégot B, Vo-Thanh G, Gori D, Loupy A (2004) Tetrahedron Lett 45:6425
Gausephol R, Buskens P, Kleinen J, Bruckmann A, Lehmann CW, Klankermayer J, Leitner W (2006) Angew Chem Int Ed 45:3689
Kitazume T (2001) 0,031,875, US
Xie Y-Y, Chen Z-C, Zheng Q-G (2002) Synthesis 1505
Liu Z, Chen Z-C, Zheng Q-G (2004) Synthesis 33
Siddiqui SA, Nadaf RN, Rajagoal R, Daniel T, Lathoti RJ, Srinivasan KV (2004) Synth Commun 34:41
Kotti SRSS, Xu X, Li G, Headley AD (2004) Tetrahedron Lett 45:1427
Yoo K, Namboodin VV, Varma RS, Smirniotis PG (2004) J Catal 511
Douelle F, Tal L, Greaney MF (2005) Chem Commun 660
Wang H-M, Hou R-S, Huang H-Y, Chen L-C (2006) Heterocycles 68:1651
Imori S, Togo H (2006) Synlett 2629
Zheng ZQ, Wang J, Wu TH, Zhou XP (2007) Adv Synth Catal 349:1095
Yang L, Xu LW, Zhou W, Li L, Xia C-G (2006) Tetrahedron Lett 47 7723
Xu J-M, Wu W-B, Qian C, Liu B-K, Lin X-F (2006) Tetrahedron Lett 47:1555
Chen J, Wu H, Jin C, Zhang X, Xie Y, Su W (2006) Green Chem 8:330
Meshram HM, Reddy PN, Vishnu P, Sadashiv K, Yadav JS (2006) Tetrahedron Lett 47:991
Xu L-W, Li L, Xia C-G, Zhao P-Q (2004) Tetrahedron Lett 45:2435
Das B, Chowdhury N, Damodar K (2007) Tetrahedron Lett 48:2867
Bandgar BP, Shaikh KA (2003) Tetrahedron Lett 44:1959
Das B, Banerjee J, Ramu R, Pal R, Ravindranath N, Ramesh C (2003) Tetrahedron Lett 44:5465
Ramalinga K, Vijayalakshmi P, Kaimal TNB (2002) Tetrahedron Lett 43:879
Firouzabadi H, Iranpoor N, Hazarkhani H (2001) J Org Chem 66:7527
Gao S, Tzeng T, Sastry MNV, Chu C-M, Liu J-T, Lin C, Yao C-F (2006) Tetrahedron Lett 47:1889
Xia M, Lu Y-D (2005) Synlett 2357
Varala R, Nuvula S, Adapa SR (2006) J Org Chem 71:8283
Yadav JS, Reddy BVS, Rao CV, Reddy MS (2003) Synthesis 247
Periana RA, Mirinov O, Taube DJ, Gamble S (2002) Chem Commun 2376
Das B, Reddy KR, Ramu R, Thirupathi P, Ravikanth B (2006) Synlett 1756
Phukan P (2004) J Org Chem 69:4005
Basu MK, Samajdar S, Becker FF, Banik BK (2002) Synlett 319
Sakakura A, Ukai A, Ishihara K (2007) Nature 445:900
Masaki Y, Miura T, Ochiai M (1996) Bull Chem Soc Jpn 69:195
Masaki Y, Miura T (1995) Synth Commun 25:1981
Masaki Y, Miura T (1995) Tetrahedron 51:10477
Masaki Y, Tanaka N, Miura T (1998) Tetrahedron Lett 39:5799
Tanaka N, Masaki Y (1999) Synlett 1277
Tanaka N, Masaki Y (2000) Synlett 406
Denmark SE, Collins WR (2007) Org Lett 9:3801
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Sereda, O., Tabassum, S., Wilhelm, R. (2010). Lewis Acid Organocatalysts. In: List, B. (eds) Asymmetric Organocatalysis. Topics in Current Chemistry, vol 291. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-02815-1_17
Download citation
DOI: https://doi.org/10.1007/978-3-642-02815-1_17
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-02814-4
Online ISBN: 978-3-642-02815-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)