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Dynamic Kinetic Resolution in the Asymmetric Synthesis of β‐Amino Acids by Organocatalytic Reduction of Enamines with Trichlorosilane
Author(s) -
Malkov Andrei V.,
Stončius Sigitas,
Vranková Kvetoslava,
Arndt Matthias,
Kočovský Pavel
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801244
Subject(s) - enamine , chemistry , imine , trichlorosilane , valine , organocatalysis , reduction (mathematics) , amino acid , catalysis , combinatorial chemistry , enantioselective synthesis , organic chemistry , biochemistry , mathematics , geometry , silicon
Resolved dynamically : A new, expedient protocol has been developed for the asymmetric synthesis of β 3 ‐ and β 2, 3 ‐amino acid derivatives from enamine precursors (see scheme). The method relies on a fast equilibrium between the enamine and imine forms. Reduction of the imine with Cl 3 SiH, catalyzed by the L ‐valine‐derived formamide L* (5 mol %), afforded the corresponding amino esters in good yields, good enantioselectivities (≤90 % ee ) and high diastereoselectivities (≤99 % de ).