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An Unprecedented Silver Salt Effect Switches the Facial Selectivity in the Vinylogous Mukaiyama Aldol Reaction
Author(s) -
Liang Yufan,
Wang Lin,
Zhu Rong,
Deng Lujiang,
Yang Yunfang,
Quan Junmin,
Chen Jiahua,
Yang Zhen
Publication year - 2010
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.201000420
Subject(s) - aldol reaction , chemistry , selectivity , silylation , acetal , salt (chemistry) , organic chemistry , chloride , aldol condensation , glyoxylate cycle , combinatorial chemistry , catalysis , enzyme
Silver hexafluroantimonate was identified as a highly efficient agent to reverse the facial selectivity of the titanium chloride‐mediated vinylogous Mukaiyama aldol reaction (VMAR), and this unprecedented reaction provides a concise, diastereoselective synthesis of δ‐hydroxy‐α,γ‐dimethyl‐α,β‐unsaturated carbonyl units from readily available chiral vinylketene silyl N , O ‐acetal 6 and ethyl glyoxylate 8 .
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