Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8783-8786

  Shibata, Takanori ^a   Morioka, Hiroshi ^a   Tanji, Shigehisa ^a   Hayase, Tadakatsu ^a   Kodaka, Yasutaka ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; PYRIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030602193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02031-X     Document Type: Article

References (19)

1. 1 For the implications of asymmetric autocatalysis: Wynberg, H. J. Macromol, Sci. Chem., 1989, A26, 1033-1041.
2. 2 Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun., 1990, 982-983.
3. 11 using 1.0 equivalent of DIBAL-H at -100 °C. (formula presented)
4. 4 Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem., 1991, 56, 4264-4268.
5. 5 Reviews: Soai, K.; Niwa, S. Chem. Rev., 1992, 92, 833-856; Soai, K.; Hayase, T. J. Synth. Org. Chem. Jpn., 1995, 53, 138-150; Noyori, R.; Kitamura, M. Angew. Chem., 1991, 103, 34-55.
6. 5 Reviews: Soai, K.; Niwa, S. Chem. Rev., 1992, 92, 833-856; Soai, K.; Hayase, T. J. Synth. Org. Chem. Jpn., 1995, 53, 138-150; Noyori, R.; Kitamura, M. Angew. Chem., 1991, 103, 34-55.
7. 5 Reviews: Soai, K.; Niwa, S. Chem. Rev., 1992, 92, 833-856; Soai, K.; Hayase, T. J. Synth. Org. Chem. Jpn., 1995, 53, 138-150; Noyori, R.; Kitamura, M. Angew. Chem., 1991, 103, 34-55.
8. 6 Soai, K.; Hayase, T.; Takai, K.; Sugiyama, T. J. Org. Chem., 1994, 59, 7908-7908.
9. 3 (15 ml) at 0 °C. The mixture was filtered using celite and the filtrate was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. Purification of the crude products on silica gel TLC (thin-layer chromatography) gave 2a (82.9 mg), which is a mixture of the newly formed alcohol 2a and the catalyst alcohol (27.4 mg). HPLC analysis of the mixture using a chiral column (DAICEL CIRALPAK AS, eluent: 5% 2-propanol in hexane; flow rate: 1.0 ml/min; 254 nm UV detector) showed that it had an enantiomeric purity of 75.4% e.e. Therefore, the mixture contained (S)-isomer (72.7 mg) and (R)-isomer (10.2 mg). The amount of newly-formed alcohol 2a was 82.9-27.4=55.5 mg (0.38 mmol, 76% yield), consisting of the major (S)-isomer (72.7-26.1=46.6 mg) and the minor (R)-isomer (10.2-1.3=8.9 mg). Therefore, the newly-formed (S)-enriched alcohol 2a had an enantiomeric purity of 67.9% e.e.
10. 8 Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry, 1994, 5, 789-792; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry, 1995, 6, 637-638; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc., 1996, 118, 471-472; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun., 1996, 751-752.
11. 8 Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry, 1994, 5, 789-792; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry, 1995, 6, 637-638; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc., 1996, 118, 471-472; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun., 1996, 751-752.
12. 8 Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry, 1994, 5, 789-792; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry, 1995, 6, 637-638; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc., 1996, 118, 471-472; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun., 1996, 751-752.
13. 8 Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry, 1994, 5, 789-792; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry, 1995, 6, 637-638; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc., 1996, 118, 471-472; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun., 1996, 751-752.
14. 9 ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. I, 1993, 885-886;
15. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber., 1992, 125, 1191-1203. For asymmetric autoinduction, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc., 1989, 111, 7265-7266; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem., 1991, 56, 6740-6741.
16. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber., 1992, 125, 1191-1203. For asymmetric autoinduction, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc., 1989, 111, 7265-7266; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem., 1991, 56, 6740-6741.
17. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber., 1992, 125, 1191-1203. For asymmetric autoinduction, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc., 1989, 111, 7265-7266; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem., 1991, 56, 6740-6741.
18. 10 West, A. P.; Silverman, S. K.; Dougherty, D. A. J. Am Chem. Soc., 1996, 118, 1452-1463.
19. 11 Nahm, S.; Weinreb, S. M. Tetrahedron Lett., 1981, 22, 3815-3818.