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Enantioselective Addition of Silicon Nucleophiles to Aldimines Using a Preformed NHC–Copper(I) Complex as the Catalyst
Author(s) -
Hensel Alexander,
Nagura Kazuhiko,
Delvos Lukas B.,
Oestreich Martin
Publication year - 2014
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.201402086
Subject(s) - aldimine , enantioselective synthesis , nucleophile , catalysis , silicon , chemistry , ligand (biochemistry) , copper , carbene , alkoxide , organic chemistry , nucleophilic addition , polymer chemistry , combinatorial chemistry , biochemistry , receptor
A remaining major challenge in the asymmetric addition of silicon nucleophiles to typical prochiral acceptors, the enantioselective 1,2‐addition to aldimines, is addressed. Activation of the SiB bond in the silicon pronucleophile by a copper(I) alkoxide with McQuade’s chiral six‐membered N‐heterocyclic carbene as a supporting ligand releases the silicon nucleophile, which adds to various aldimines with high levels of enantioselectivity. The new method provides a catalytic asymmetric access to α‐silylated amines.