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From Protected β ‐Hydroxy Acylsilanes to Functionalized Silyl Enol Ethers and Applications in Mukaiyama Aldol Reactions
Author(s) -
Ruiz Johal,
Karre Nagaraju,
Roisnel Thierry,
Chandrasekhar Srivari,
Grée René
Publication year - 2016
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.201501344
Subject(s) - aldol reaction , chemistry , enol , silylation , moiety , silyl enol ether , enol ether , silyl ether , organic chemistry , stereochemistry , catalysis
By starting from protected β‐hydroxy acylsilanes, two complementary strategies were designed to prepare stereoselectively either E or Z silyl enol ethers. These routes exhibit good tolerance for different substituents on the starting aldol‐type product, as well as the choice of the hydroxyl‐protecting group and the acylsilane moiety. Further, by varying the nature of the sulfone used in these reactions it proved possible to introduce different substituents on the enol ether system. Representative examples of Mukaiyama aldol reactions were performed to demonstrate the usefulness of this approach towards polypropionate fragments.