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Stereoselective Synthesis of Highly Substituted α‐Silylamines from Silylmethyl Azides under Ru Catalysis
Author(s) -
Jeong Wook,
Kim Jungjoon,
Park Jaiwook,
Rhee Young Ho
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403200
Subject(s) - chemistry , stereocenter , iminium , silylation , azide , moiety , stereoselectivity , combinatorial chemistry , hydride , catalysis , organic chemistry , enantioselective synthesis , metal
A synthetic strategy towards highly substituted α‐silyl homoallylic amines was discovered. The key event is the unique synthesis of N ‐unsubstituted α‐silylimines from azide precursors under mild conditions. Of particular note is the unprecedented access to α‐silylamines possessing multiple stereocenters and functional groups with high diastereo‐ and enantioselectivity. The synthetic utility of the method was demonstrated by the use of the silyl moiety as the key element that enables late‐stage modification for the iminium ion mediated oxidative cyclization.