A Novel Highly Effective Chiral Lithium Amide for Catalytic Enantioselective Deprotonation of meso-Epoxides

A highly enantioselective deprotonation of meso-epoxides was achieved by a catalytic amount of a new chiral lithium amide, derived from (2 S,3a S,7a S)-2-(pyrrolidin-1-ylmethyl)octahydroindole, in the presence of excess lithium diisopropylamide to afford the corresponding allylic alcohol derivatives...

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Bibliographic Details
Published in:Tetrahedron letters 1997-09, Vol.38 (36), p.6425-6428
Main Authors: Asami, Masatoshi, Suga, Takashi, Honda, Kiyoshi, Inoue, Seiichi
Format: Article
Language:English
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Summary:A highly enantioselective deprotonation of meso-epoxides was achieved by a catalytic amount of a new chiral lithium amide, derived from (2 S,3a S,7a S)-2-(pyrrolidin-1-ylmethyl)octahydroindole, in the presence of excess lithium diisopropylamide to afford the corresponding allylic alcohol derivatives up to 94% ee. © 1997 Elsevier Science Ltd.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01487-1