Asymmetric self-replication of chiral 1,2-amino alcohols by highly enantioselective autoinductive reduction

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 22, 1997, Pages 2458-2460

  Shibata, Takanori ^a   Takahashi, Tomohide ^a   Konishi, Takashi ^a   Soai, Kenso ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Amino alcohols; Asymmetric synthesis; Hydrides; Reductions

Indexed keywords

EID: 0031470261     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199724581     Document Type: Article

References (26)

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21. See the Experimental Section for details on how the amount of newly formed 2 a was calculated.
22. In these reactions, lowering the reaction temperature had no significant effect on the yield or ee value.
23. No distinct amplification of the ee value was observed for (S)-2d (51.7% ee) when (S)-2d with lower ee (51.4% ee) was used.
24. Amino alcohol (S)-2f was prepared by asymmetric reduction of α-amino ketone 1f with chirally modified lithium borohydride: K. Soai, S. Niwa, T. Kobayashi, J. Chem. Soc. Chem. Commun. 1987, 801-802; recent examples of asymetric reduction of α-amino ketones for the preparation of chiral 1,2-amino alcohols: B. T. Chao, Y. S. Chun, Tetrahedron: Asymmetry 1992, 3, 341-342; G. J. Quallich, T. M. Woodall, Tetrahedron Lett. 1993, 34, 4145-4148.
25. Amino alcohol (S)-2f was prepared by asymmetric reduction of α-amino ketone 1f with chirally modified lithium borohydride: K. Soai, S. Niwa, T. Kobayashi, J. Chem. Soc. Chem. Commun. 1987, 801-802; recent examples of asymetric reduction of α-amino ketones for the preparation of chiral 1,2-amino alcohols: B. T. Chao, Y. S. Chun, Tetrahedron: Asymmetry 1992, 3, 341-342; G. J. Quallich, T. M. Woodall, Tetrahedron Lett. 1993, 34, 4145-4148.
26. Amino alcohol (S)-2f was prepared by asymmetric reduction of α-amino ketone 1f with chirally modified lithium borohydride: K. Soai, S. Niwa, T. Kobayashi, J. Chem. Soc. Chem. Commun. 1987, 801-802; recent examples of asymetric reduction of α-amino ketones for the preparation of chiral 1,2-amino alcohols: B. T. Chao, Y. S. Chun, Tetrahedron: Asymmetry 1992, 3, 341-342; G. J. Quallich, T. M. Woodall, Tetrahedron Lett. 1993, 34, 4145-4148.