Skip to main content
SpringerLink
Log in

Asymmetric Reduction

  • Chapter
Hydroboration and Organic Synthesis

  • 2022 Accesses

Abstract

The synthesis of optically active compounds is challenging problem before organic chemists. The main interest lies in the biologically active and pharmaceutical compounds. A large number of drugs, agrochemicals, food additives, and flavoring agents are being prepared by total synthesis. The racemic compounds thus formed in the course of reaction sequence are normally resolved at the end of the synthesis. This procedure thus leads to the wastage of half of the synthetic product, which is discarded. Moreover, resolution is usually a tedious and laborious process.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. (a) Le Bel JA (1874) Bull Soc Chim Fr 22:337, 11; Le Bel JA (1894) Bull Soc Chim Fr 22:295; (b) van’t Hoff JH (1975) La Chimie dans L’Espace. Bazendijk, Rotterdan, The Netherlands, p 13–14; Bull Soc Chim Fr 23:295. English translations of both Le Bel and van’t Hoff’s work are available: Richardson GM (ed) (1901) The foundation of stereochemistry. American Book, New York; Benfey OT (ed) (1963) Classics in theory of chemical combinations. In: Classics of science, vol. 1. Dover, New York, reprinted (1981) by Krieger, Malabar, Florida

    Google Scholar 

  2. Fischer E (1984) Chem Ber 27:3231

    Google Scholar 

  3. Thalidomide is an excellent example of drug whose S-isomer possesses teratogenic activity, while the R-isomer is potent mutagen. Blaschke G, Kraft HP, Fickentscher K, Koehler F (1979) Arzneim Forsch 29:1640; Blaschke G, Kraft HP, Markgraf H (1980) Chem Ber 113,:2318

    CAS  Google Scholar 

  4. (a) Morrison JD, Mosher HS (1971) Asymmetric organic reactions. Prentice Hall, New York; (b) Valentine D Jr, Scott JW (1978) Synthesis 329; (c) ApSimon JW, Seguin RP (1979) Tetrahedron 35:2797; (d) Kagan HB, Fiaud JC (1978) Top Stereochem 10:175; (e) Brown HC, Jadhav PK, Mandal AK (1981) Tetrahedron 37:3547; (f) Corey EJ, Guzman-Perez A (1998) Angew Chem Int Ed 37:37

    Google Scholar 

  5. Brown HC, Pai GG (1985) J Org Chem 50:1384

    Article  CAS  Google Scholar 

  6. Mosher HS, Morrison JD (1983) Science 221:1013. For an extensive review of the asymmetric synthesis, see Morrison, JD (ed) Asymmetric synthesis, vols. 1–4. Academic, New York; (a) Imai T, Tamura T, Yamamuro A, Sato T, Wollmann TA, Kennedy RM, Masamune S (1986) J Am Chem Soc 108:7402; (b) Corey EJ, Bakshi RK, Shibata S (1987) ibid. 109:5551; (c) Corey EJ, Bakshi RK, Shibata S, Chen C-P, Singh, V K (1987) ibid. 109:7925. (d) Itsuno S, Nakano M, Miyazaki K, Masuda H, Ito K, Hirao A, Nakahama S (1985) J Chem Soc Perkin Trans I 2039; (e) Itsuno S, Nakano M, Ito K, Hirao A, Owa M, Kanda N, Nadahama S (1985) ibid. 2615. (f) Brown HC, Chandrasekharan J, Ramachandran PV (1988) J Am Chem Soc 110:1539. (g) Brown HC, Cho BT, Park WS (1988) J Org Chem 53:1231 and references within these papers; (h) For a comparison of relative effectiveness of various reducing agents, see Brown HC, Park WS, Cho BT, Ramachandran PV (1987) J Org Chem 52:5406; (i) Mikhailov BM, Bubnov YN, Kiselev VG (1966) J Gen Chem USSR 36:65; (j) Corey EJ, Helal CJ (1998) Angew Chem Int Ed 37:1986

    Article  ADS  CAS  Google Scholar 

  7. Mikhailov B, Bobnov YN, Kiselev VG (1966) J Gen USSR 36:65; Midland MM, Zderic SA (1982) J Am Chem Soc 104:525

    Google Scholar 

  8. Brown HC, Subba Rao BC (1956) J Am Chem Soc 78:2582. For reviews of the uses of organoboranes in synthesis, see (b) Brown HC (1962) Hydroboration. Benjamin, New York; (c) Brown HC (1972) Boranes in organic chemistry. Cornell University, Ithaca, New York. (d) Brown HC, Kramer GW, Levy AB, Midland MM (1975) Organic synthesis via boranes. Wiley InterScience, New York

    Article  CAS  Google Scholar 

Section 26.1.1

  1. Arigoni D, Eliel EL (1969) In: Eliel EL, Allinger NL (eds) Topics in stereochemistry, vol 4. Wiley InterScience, New York, pp 127–244; Verbit L (1970) In: Streitweiser R, Taft RW (eds) Progress in physical organic chemistry, vol. 7. Wiley InterScience, New York, p 51-127; Lau KSY, Wong PK, Stille JK (1976) J Am Chem Soc 98 (1976) 5832; Caspi E, Eck CR (1977) J Org Chem 42:767 references cited therein

    Chapter  Google Scholar 

  2. (a) Althouse VE, Feigl DM, Sanderson WA, Mosher HS (1966) J Am Chem Soc 88:3595; (b) Varma KR, Caspi E (1968) Tetrahedron 24:6365; (c) Wolfe S, Rauk A (1966) Can J Chem 44:2591; (d) Reich CJ, Sullivan GR, Mosher HS (1973) Tetrahedron Lett 1505; (e) Streitwieser A Jr, Wolfe JR Jr, Shaeffer WD (1959) Tetrahedron 6:338; (f) Gerlach H (1966) Helv Chim Acta 49:2481

    Article  PubMed  CAS  Google Scholar 

  3. Midland MM, Tramontano A, Zderic SA (1978) J Organomet Chem 156:203

    Article  CAS  Google Scholar 

  4. Midland MM, Tramontano A, Zderic SA (1977) J Organomet Chem 134:C17

    Article  CAS  Google Scholar 

  5. Midland MM, Tramontano A, Zderic SA (1977) J Am Chem Soc 99:5211

    Article  CAS  Google Scholar 

  6. Burgstahler AW, Walker DE Jr, Kuebrich JP, Schowen RL (1972) J Org Chem 37:1272. Also see Chancellor T, Quill M, Bergbreiter DE, Newcolmb MV (1978) ibid. 43:1245; Seebeck D, Erickson BW, Singh L (1966) ibid. 31:4303

    Article  CAS  Google Scholar 

  7. Krishnamurty S, Brown HC (1977) J Org Chem 42:1197

    Article  Google Scholar 

  8. Midland MM, Greer S, Tramontano A, Zderic SA (1979) J Am Chem Soc 101:2352

    Article  CAS  Google Scholar 

  9. B-3-Pinanyl-9-borabicyclo[3.3.1]nonane is commercially available from Aldrich Chemical Co. under the trademark Alpine-Borane.

    Google Scholar 

  10. (a) Brown HC, Yoon MM (1977) Isr J Chem 15:12.; (b) Brown HC, Jadhav PK, Desai MC (1982) J Org Chem 47:4583

    CAS  Google Scholar 

  11. Midland MM, Tramontano A (1978) J Org Chem 43:1470

    Article  CAS  Google Scholar 

  12. Midland MM, Petre JE, Zderic SA (1979) J Organomet Chem 182:653

    Article  Google Scholar 

  13. Parry RJ, Trainor DA (1978) J Am Chem Soc 100:5243

    Article  CAS  Google Scholar 

Section 26.1.2

  1. (a) Midland MM, Tramontano A, Zderic SA (1977) J Am Chem Soc 99:5211; (b) Midland MM, Greer S, Tramontano A, Zderic SA (1979) ibid. 101:2352; (c) Midland MM, McDowell DD, Hatch RL, Tramontano A (1980) ibid. 102:867; (d) Midland MM, Tramontano A, Kazubski A, Graham RS, Tsai DJS, Cardin DB (1984) Tetrahedron 40:1371

    Article  CAS  Google Scholar 

  2. (a) Midland MM, Petre JE, Zderic SA, Kazubski A (1982) J Am Chem Soc 104:528; (b) Midland MM, Tramontano A, Zderic SA (1977) J Organomet Chem C17:134; Midland MM, Tramontano A, Zderic SA (1978) ibid. 156:203

    Article  CAS  Google Scholar 

  3. Brown HC, Pai GG (1985) J Org Chem 50:1384

    Article  CAS  Google Scholar 

  4. (a) Brown HC, Pai GG (1983) J Org Chem 48:1784; (b) Brown HC, Pai GG, Jadhav PK (1984) J Am Chem Soc 106:1531; (c) Midland MM, Lee PE (1985) J Org Chem 50:3237

    Article  CAS  Google Scholar 

  5. Brown HC, Pai GG (1982) J Org Chem 47:1606

    Article  CAS  Google Scholar 

  6. Midland MM, Zderic SA (1982) J Am Chem Soc 104:525

    Article  CAS  Google Scholar 

  7. Midland MM, McLoughlin JI, (1984) J Org Chem 49:1316

    Article  CAS  Google Scholar 

  8. Midland MM, McLoughlin JI, Gabriel J (1989) J Org Chem 54:159

    Article  CAS  Google Scholar 

  9. Krishnamurthy, S, Brown HC (1977) J Org Chem 42:1197

    Article  CAS  Google Scholar 

  10. Ranieri RL, McLaughlin JL (1977) Lloydia 40:173

    PubMed  CAS  Google Scholar 

  11. (a) Cohen N, Lopresti RJ, Neuekom C, Saucy G (1980) J Org Chem 45:582; (b) Brinkmeyer RS, Kapoor VM (1977) J Am Chem Soc 99:8339; (c) Vigneron JP, Bloy V (1979) Tetrahedron Lett 2683; (d) Mukaiyama T, Suzuki K, Soai K, Sato T (1979) Chem Lett 447; (e) Noyori R, Nishizawa M, Yamada M (1981) Tetrahedron Lett 22:247

    Article  CAS  Google Scholar 

  12. (a) Overman LE, Bell KL (1981) J Am Chem Soc 103:1851; (b) Pirkle WH, Boeder CW (1978) J Org Chem 43:2091; (c) Fried J, Sih JC, Lin CH, Dalven P, Cooper GF (1972) J Am Chem Soc 94:4343; (d) Fried J, Lin CH (1973) J Med Chem 16:429; (e) Partridge JJ, Chadha, NK, Uskokovic MR (1973) J Am Chem Soc 95:7171; (f) Fried J, Sih JC (1973) Tetrahedron Lett 3899; (g) Johnson WS, Frei B, Gopalan AS (1981) J Org Chem 46:1512; (h) Chan K, Specian AC Jr, Saucy G (1978) ibid. 43:3435; (i) Stork G, Poinier JM (1983) J Am Chem Soc 105:1073

    Article  CAS  Google Scholar 

  13. Midland MM, McDowell DC, Hatch RL, Tramontano A (1980) J Am Chem Soc 102:867

    Article  CAS  Google Scholar 

  14. (a) Midland MM, Tramontano A, Kuzubski A, Graham RS, Tsai DJS, Cardin DB (1984) Tetrahedron 40:1371

    Article  CAS  Google Scholar 

  15. Midland MM, Tramontano A (1978) J Org Chem 43:1470

    Article  CAS  Google Scholar 

  16. Midland MM, Halterman RL, Brown CA, Yamaichi A (1981) Tetrahedron Lett 22:4171

    Article  CAS  Google Scholar 

  17. (a) Cohen N, Lopresti RJ, Neukom C, Saucy G (1980) J Org Chem 45:582, and refs therein; (b) Johnson WS, Werthemann L, Bartlett WR, Brocksom TJ, Li TT, Faulkner DJ, Peterson MR (1970) J Am Chem Soc 92:741; (c) Hirano Y, Djerassi C (1982) J Org Chem 47:2420

    Article  CAS  Google Scholar 

  18. Sardina FJ, Mourino A, Castedo L (1983) Tetrahedron Lett 24:4477

    Article  CAS  Google Scholar 

  19. Midland MM, Kwon YC (1984) Tetrahedron Lett 25:5981

    Article  CAS  Google Scholar 

  20. Midland MM, McDowell DC, Hatch RL, Tramontano A (1980) J Am Chem Soc 102:867

    Article  CAS  Google Scholar 

  21. Satoh T, Suzuki S, Suzuki Y, Miyaji Y, Imai Z (1969) Tetrahedron Lett 4555

    Google Scholar 

Section 26.2

  1. (a) Midland MM, Kazubski A (1982) J Org Chem 47:2814; (b) Midland MM, Tramontano A, Kazubski A, Graham RS, Tsai DJS, Cardin DB (1984) Tetrahedron 40:1371

    Article  CAS  Google Scholar 

  2. NB-Enantrane is a trademark of Aldrich Chemical Co. Nopol is also available from Aldrich Chemical Co.

    Google Scholar 

  3. Midland MM, McDowell DC, Hatch RL, Tramontano A (1980) J Am Chem Soc 102:867

    Article  CAS  Google Scholar 

Section 26.3

  1. Brown HC, Ramachandran PV, Weissman SA, Swaminathan S (1990) J Org Chem 55:6328

    Article  CAS  Google Scholar 

  2. Brown HC, Ramachandran PV (1989) J Org Chem 54:4504

    Article  CAS  Google Scholar 

  3. Brown HC, Pai GG (1985) J Org Chem 50:1384

    Article  CAS  Google Scholar 

  4. Brown HC, Randad RS, Bhat KS, Zaidlewicz M, Weissman SA, Jadhav PK, Perumal PT (1988) J Org Chem 53:5513

    Article  CAS  Google Scholar 

  5. Johnson CR, Dutra CR (1973) J Am Chem Soc 95:7777

    Article  CAS  Google Scholar 

Section 26.4

  1. Krishnamurthy S, Vogel F, Brown HC (1977) J Org Chem 42:2534

    Article  CAS  Google Scholar 

  2. Midland MM, Kazubski A (1982) ibid. 47:2495

    Article  CAS  Google Scholar 

  3. The reagent is available from Aldrich under the trademark NB-Enantride

    Google Scholar 

  4. Brown HC, Pai GG (1982) J Org Chem 47:1606

    Article  CAS  Google Scholar 

  5. Midland MM, Kazubski A, Woodling RE (1991) J Org Chem 56:1068

    Article  CAS  Google Scholar 

  6. Brown HC, Randad RS, Bhat KS, Zaidlewicz M, Weissman SA, Jadhav PK, Perumal PT (1988) J Org Chem 53:5513

    Article  CAS  Google Scholar 

Section 26.5

  1. Ramachandran PV, Brown HC, Swaminathan S (1990) Tetrahedron Asym 1:433

    Article  CAS  Google Scholar 

Section 26.6

  1. Brown HC, Cha JS, Nazer B (1984) J Org Chem 49:2073

    Article  CAS  Google Scholar 

  2. Brown HC, Cha JS, Nazer B, Brown CA (1985) J Org Chem 50:549

    Article  Google Scholar 

  3. (a) Brown HC, Park WS, Cho BT (1986) J Org Chem 51:3278; (b) Brown HC, Park WS, Cho BT (1987) Bull Korean Chem Soc 8:2, 211; (c) Brown HC, Park WS, Cho BT (1987) ibid. 8:276

    Article  CAS  Google Scholar 

  4. Brown HC, Park WS, Cho BT (1986) J Org Chem 51:1934

    Article  CAS  Google Scholar 

  5. Hirao A, Itsuno S, Owa M, Nagami S, Mochizuki H, Zoorov HHA, Niakahama S, Yamazaki M (1981) J Chem Soc Perkin Trans I 900

    Google Scholar 

  6. Brown HC, Cho BT, Park WS (1986) J Org Chem 51:3396

    Article  CAS  Google Scholar 

  7. Brown HC, Cho BT, Park WS (1988) J Org Chem 53:1231

    Article  CAS  Google Scholar 

  8. Noyori R, Tomino I, Tanimoto, Y, Nishizawa M (1984) J Am Chem Soc 106:6709; Noyori R, Tomino I, Yamada M, Nishizawa M (1984) ibid. 106:6717

    Article  CAS  Google Scholar 

  9. Brown HC, Pai GG, Jadhav PK (1984) J Am Chem Soc 106:1531; (b) Brown HC, Pai GG (1985) J Org Chem 50:1384; (c) Midland MM, Zderic SA (1982) J Am Chem Soc 104:525

    Article  CAS  Google Scholar 

Section 26.7

  1. Cho BT, Chun YS (1992) Tetrahedron Asym 3:73

    Article  CAS  Google Scholar 

  2. Cho BT (1990) J Korean Chem Soc 34:313

    CAS  Google Scholar 

  3. For ketones see Brown HC, Park WS, Cho BT, Ramachandran PV (1987) J Org Chem 52:5406

    Article  CAS  Google Scholar 

  4. Shah RH, Schaeffer HJ, Murray DH (1965) J Pharm Sci 54:15

    Article  PubMed  CAS  Google Scholar 

Section 26.8

  1. Brown HC, Cha JS, Nazer B (1984) J Org Chem 49:2073

    Article  CAS  Google Scholar 

  2. Brown HC, Krishnamurthy S (1972) J Am Chem Soc 94:7159

    Article  CAS  Google Scholar 

Section 26.9

  1. Yamamoto Y, Toi H, Sonoda A, Murahashi S-I (1976) J Am Chem Soc 98:1965

    Article  CAS  Google Scholar 

  2. (a) Yamamoto Y, Toi H, Murahashi S-I, Moritani I (1975) J Am Chem Soc 97:2558; (b) Damico R (1964) J Org Chem 29:1971

    Article  CAS  Google Scholar 

Section 26.10

  1. Brown HC, Singaram B, Mathew CP (1981) J Org Chem 46:2712

    Article  CAS  Google Scholar 

  2. Brown HC, Mathew CP, Pyun C, Son JC, Yoon NM (1984) J Org Chem 49:3091

    Article  CAS  Google Scholar 

  3. Brown HC, Krishnamurthy S, Yoon NM (1975) J Org Chem 40:1864

    Article  Google Scholar 

Section 26.11

  1. Brown HC, Park WS, Cho BT, Ramachandran PV (1987) J Org Chem 52:5406

    Article  CAS  Google Scholar 

  2. Reagent A, B-Ipc-9-BBN, THF. This reagent is available from Aldrich Chemical Co. as Alpine-Borane: (a) Midland MM, Greer, S, Tramontano A, Zderic SA (1979) J Am Chem Soc 101:2352; (b) Midland MM, Tramontano A, Kazubski A, Graham RS, Tsai DJS, Cardin DB (1984) Tetrahedron 40:1371; (c) Tramontano A (1980) Ph.D. Thesis, University of California, Riverside

    Article  CAS  Google Scholar 

  3. Reagent B, B-Ipc-9-BBN, neat: (a) Brown HC, Pai GG (1982) J Org Chem 47:1606; (b) Brown HC, Pai GG (1983) ibid. 48:1784; (c) Brown HC, Pai GG, Jadhav PK (1984) J Am Chem Soc 106:1531: (d) Brown HC, Pai GG (1985) J Org Chem 50:1384

    Article  CAS  Google Scholar 

  4. Reagent C, B-Ipc-9-BBN,6 kbar: Midland MM, McLoughlin JI (1984) J Org Chem 49:1316

    Article  CAS  Google Scholar 

  5. Reagent D, NB-Enantrane is a registered trademark of Aldrich Chemical Co. Midland MM, Kazubski A (1982) J Org Chem 47:2814

    Article  CAS  Google Scholar 

  6. Reagent E, Ipc2BCl, is available from Aldrich Chemical Co. (a) Chandrasekharan J, Ramchandran PV, Brown HC (1985) J Org Chem 50:5446; (b) Brown HC, Chandrasekharan J, Ramachandran PV (1986) ibid. 51:3394

    Article  CAS  Google Scholar 

  7. Reagent F, BH3-AMDPB (2:1), AMDPB=(S)-(-)-2-amino-1,1-diphenyl butan-1-ol: (a) Hirao A, Itsuno S, Nakahama S, Yamazaki N (1981) J Chem Soc Chem Commun 315; (b) Itsuno S, Ito K, Hirao A, Nakahama S (1983) ibid. 469; (c) Itsuno S, Hirao A, Nakahama S, Yamazaki N (1983) J Chem Soc Perkin Trans I 1673; (d) Itsuno S, Ito K, Hirao A, Nakahama S (1984) J Org Chem 49:555; (e) Itsuno S, Nakano M, Miyazaki K, Masuda H, Ito K, Hirao A, Nakahama S (1985) J Chem Soc Perkin Trans I 2039

    Google Scholar 

  8. Reagent G, (R,R)-2-5-Dimethylborolane: Imai T, Tamura T, Yamamuro A, Sato T, Wollman TA, Kennedy RM, Masamune S (1986) J Am Chem Soc 108:7402

    Article  CAS  Google Scholar 

  9. Reagent H, NB-Enantride, is a registered trademark of Aldrich Chemical Co. Midland MM, Kazubski A (1982) J Org Chem 47:2495

    Article  CAS  Google Scholar 

  10. Reagent I, LiBH4-DBC-t-BuOH: (a) Soai K, Oyamada H, Yamanoi T (1984) J Chem Soc Chem Commun (1984) 413; (b) Soai K, Yamanoi T, Hikima H, Oyamada H (1985) ibid. 138

    Google Scholar 

  11. Reagent J, NaBH4-IBA-DIPGF, IBA = isobutyric acid, DIPGF = 1, 2:5, 6-di-O-isopropylidene-α-D-glucofuranose: (a) Hirao A, Itsuno S, Owa M, Nagami S, Mochizuki H, Zoorov HHA, Niakahama S, Yamazaki N (1981) J Chem Soc Perkin Trans I 900; (b) Morrison JD, Grandbois ER, Howard SI (1980) J Org Chem 45:4229

    Google Scholar 

  12. Reagent K, K-glucoride, potassium 9-O-(1,2,5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane: (a) Brown HC, Park WS, Cho BT (1986) J Org Chem 51:1934; (b) Brown HC, Park WS, Cho BT (1986) ibid. 3278; (c) Brown HC, Cho BT, Park WS (1986) ibid. 3396

    Article  CAS  Google Scholar 

  13. Reagent L, LiAlH4-Darvon Alc, Darvon Alc=[2S,3R]-(+)-4-(dimethyl amino)-3-methyl-1,2-diphenyl-2-butanol: (a) Yamaguchi S, Mosher H, Pohland A (1972) J Am Chem Soc 94:9254; (b) Yamaguchi S, Mosher H (1973) J Org Chem 38:1870; (c) Brinkmeyer RS, Kapoor VM (1977) J Am Chem Soc 99:8339; (d) Cohen N, Lopresti RJ, Neukom C, Saucy G (1980) J Org Chem 45:582

    Article  CAS  Google Scholar 

  14. Reagent M, LiAlH4-MEP-ArOH, MEP=N-methylephedrine, ArOH-3,5-dimethylphenol: Vigneron JP, Jacquet I (1976) Tetrahedron 32:939; Vigneron JP, Bloy V (1979) Tetrahedron Lett 2683

    Article  CAS  Google Scholar 

  15. Reagent N, LiAlH4-diamine, diamine=(S)-2-(2,6-xylidinomehtyl) pyrrolidine: Asami M, Mukaiyama T (1979) Heterocycles 12:499

    Article  CAS  Google Scholar 

  16. Reagent O, LiAlH4-aminobutanol, aminobutanol=(S)-4-anilino-3-(methylamino)-1-butanol: (a) Sato T, Goto Y, Fujisawa T (1982) Tetrahedron Lett 23:4111; (b) Sato T, Gotoh Y, Wakabayashi Y, Fujisawa T (1983) ibid. 24:4123

    Article  CAS  Google Scholar 

  17. Reagent P, Binal-H: (a) Noyori R, Tomino R, Tomino I, Tanimoto Y (1979) J Am Chem Soc 101:3129; (b) Nishizawa M, Yamada M, Noyori R (1981) Tetrahedron Lett 22:247; (c) Noyori R, Tomino I, Tanimoto Y, Nishizawa M (1984) J Am Chem Soc 106:6709; (d) Noyori R, Tomino I, Yamada M, Nishizawa M (1984) ibid. 6717

    Article  CAS  Google Scholar 

  18. Reagent Q, LiAlH4-DBP-EtOH, DBP=(S)-(-)-10,10′-dihydroxy-9,9′-biphenanthryl: Yamamoto K, Fukushima H, Nakazaki M (1984) J Chem Soc Chem Commun 1490

    Google Scholar 

  19. Reagent R, LiAlH4-MEP-NEA, MEP=N-methylephedrine, NEA=N-ethylaniline: Terashima S, Tanno N, Koga K (1980) J Chem Soc Chem Commun 1026

    Google Scholar 

  20. Reagent S, LiAlH4-MEP-EAP, MEP=N-methylephedrine, EAP=2-(ethylamino)pyridine: Kawasaki M, Suzuki Y, Terashima S (1984) Chem Lett 239

    Google Scholar 

  21. Reagent T, TBADH, Thermoanaerobium brockii alcohol dehydrogenase: Keinam E, Hafeli EK, Seth KK, Lamed R (1986) J Am Chem Soc 108:162

    Article  Google Scholar 

  22. (a) Dale JA, Dull DL, Mosher HS (1969) J Org Chem 34:2543; (b) Dale JA, Mosher HS (1973) J Am Chem Soc 95:512

    Article  CAS  Google Scholar 

  23. (a) Westley JW, Halpern B (1968) J Org Chem 33:3978; (b) Pirkle WH, Hanske JR (1977) ibid. 42:2436

    Article  CAS  Google Scholar 

Download references

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

(2007). Asymmetric Reduction. In: Hydroboration and Organic Synthesis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-49076-0_26

Download citation

Publish with us

Policies and ethics

Search

Navigation