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Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes
Author(s) -
Saito Akira,
Adachi Shinya,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202016690
Subject(s) - carbene , acetonitrile , catalysis , steric effects , toolbox , chemistry , combinatorial chemistry , pincer movement , nickel , enantioselective synthesis , atom economy , organic chemistry , computer science , programming language
A direct catalytic asymmetric addition of acetonitrile to aldehydes that realizes over 90 % ee is the ultimate challenge in alkylnitrile addition chemistry. Herein, we report achieving high enantioselectivity by the strategic use of a sterically demanding Ni II pincer carbene complex, which afforded highly enantioenriched β‐hydroxynitriles. This highly atom‐economical process paves the way for exploiting inexpensive acetonitrile as a promising C2 building block in a practical synthetic toolbox for asymmetric catalysis.