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Kinetic Resolution of Acylsilane Cyanohydrins via Organocatalytic Cycloetherification
Author(s) -
Matsumoto Akira,
Asano Keisuke,
Matsubara Seijiro
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801600
Subject(s) - kinetic resolution , cyanation , optically active , chemistry , catalysis , asymmetric carbon , combinatorial chemistry , enantioselective synthesis , cyanohydrin , resolution (logic) , organic chemistry , computer science , artificial intelligence
An asymmetric cyanation of acylsilanes involving the in‐situ formation of chiral acylsilane cyanohydrins followed by their kinetic resolution via organocatalytic cycloetherification is described. The highly enantio‐ and diastereoselective cycloetherification was crucial for achieving a high efficiency in the kinetic resolution. Consequently, acylsilane cyanohydrins containing a tetrasubstituted chiral carbon atom bearing silyl, cyano, and hydroxy groups were obtained in an enantioenriched form. This protocol therefore offers an efficient catalytic approach to optically active acylsilane cyanohydrins, which exhibit potential as chiral building blocks for the synthesis of pharmaceutically relevant chiral organosilanes.