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Gold‐Catalyzed Cyclizations of Alkynyl Silyl Enol Ethers: An Easy Access to Bicyclo[3.2.1]octanone Derivatives
Author(s) -
Carrër Amandine,
Péan Christophe,
PerronSierra Françoise,
Mirguet Olivier,
Michelet Véronique
Publication year - 2016
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.201501135
Subject(s) - chemistry , enol , silylation , silyl enol ether , bicyclic molecule , catalysis , adduct , silyl ether , medicinal chemistry , ether , enol ether , organic chemistry
The efficient gold‐catalyzed cyclization reactions of alkynyl silyl enol ethers were successfully applied to the preparation of bicyclo[3.2.1]octanone derivatives. Accordingly, after optimization of the gold catalytic system, several bicyclic α,β‐unsaturated keto adducts were synthesized in good to excellent yields. The process followed a major 5‐ exo cyclization via an anti addition of the silyl enol ether to the π‐activated intermediate, which was demonstrated by a deuterium incorporation experiment. A 6‐ endo cyclization process was observed for a silyl enol ether bearing an electron‐donating aromatic group.