Premium
Cover Feature: Kinetic Resolution of Acylsilane Cyanohydrins via Organocatalytic Cycloetherification (Chem. Asian J. 1/2019)
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.201801786
Subject(s) - kinetic resolution , cyanation , chemistry , catalysis , optically active , asymmetric carbon , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry
An asymmetric cyanation of acylsilanes involving an 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 are potential chiral building blocks for the synthesis of pharmaceutically relevant chiral organosilanes. More information can be found in the Communication by Akira Matsumoto, Keisuke Asano, and Seijiro Matsubara on page 116 in Issue 1, 2019 (DOI: 10.1002/asia.201801600).