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Enantioselective Conjugate Azidation of α,β ‐Unsaturated Ketones under Bifunctional Organocatalysis by Direct Activation of TMSN 3
Author(s) -
HumbríasMartín Jorge,
PérezAguilar M. Carmen,
MasBallesté Rubén,
Dentoni Litta Antonella,
Lattanzi Alessandra,
Della Sala Giorgio,
FernándezSalas Jose A.,
Alemán José
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900831
Subject(s) - chemistry , bifunctional , enantioselective synthesis , organocatalysis , conjugate , nucleophile , hydrazoic acid , combinatorial chemistry , organic chemistry , catalysis , mathematical analysis , mathematics
An enantioselective organocatalytic conjugate azidation of α,β‐unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN 3 , triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre‐formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst.