A new approach to asymmetric synthesis of β-amino alcohols by means of α-chirally protected amino alkyllithiums

Synlett

Volumn , Issue 10, 1998, Pages 1147-1149

  Tomoyasu, Takahiro ^a   Tomooka, Katsuhiko ^b   Nakai, Takeshi ^b  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002588758     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1891     Document Type: Article

References (19)

1. (a) Jurczak, J.; Golebiowski, A. Chem. Rev., 1989, 89, 149.
2. (b) Tramontini, M. Synthesis, 1982, 605.
3. (a) Gawley, R. E.; Zhang, Q. J. Org. Chem., 1995, 60, 5763.
4. (b) Burchat, A. F.; Chong, J. M.; Park, S. B. Tetrahedron Lett., 1993, 34, 51.
5. (c) Chong, J. M.; Park, S. B. J. Org. Chem., 1992, 57, 2220.
6. (d) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 1, pp 459-485.
7. (e) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 3, pp 65-83.
8. (a) Pearson, W. H.; Lindbeck, A. C.; Kampf, J. W. J. Am. Chem. Soc., 1993, 115, 2622.
9. (b) Pearson, W. H.; Lindbeck, A. C. J. Am. Chem. Soc., 1991, 113, 8546.
10. Tomooka, K.; Igarashi, T.; Watanabe, M.; Nakai, T. Tetrahedron Lett., 1992, 33, 5795.
11. (S)-4-Phenyl-2-oxazolidinone (4) was purchased from Aldrich.
12. 3) δ 9.0, 21.7, 23.0, 24.7, 27.4, 44.7, 55.7, 84.2, 160.0.
13. 3). For instance, the δ value for CHOH, 3.45 for syn-5a and 3.64 for anti-5a. The oxidation of the diastereomer mixture of 5a with Dess-Martin periodinane was found to produce the single diastereomer of ketone 6, indicating that the two isomers were epimer at the hydroxy-bearing carbon.
14. The syn selectivity in 1,2-addition reaction can be explained as a result that the four-membered transition state A is sterically more less congested than B. (Chemical Equation Presented)
15. b: see Dufour, M-N.; Jouin, P.; Poncet, J., Pantaloni, A.; Castro, B. J. Chem. Soc. Perkin Trans 1, 1986, 1895. (Chemical Equation Presented)
16. This result suggests that the stereoselective reduction of α-amino ketone can be rationalized by applying the Felkin-Anh model.
17. Nahm, S.; Weinreb, S. M. Tetrahedron Lett., 1981, 22, 3815.
18. ab = 4.6 Hz) as described for syn-5a.
19. Begue, J-P.; Bonnet-Delpon, D; Fischer-Durand, N.; Amour, A.; Reboud-Ravaux, M. Tetrahedron: Asymmetry, 1994, 5, 1099.