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Enantioselective Conjugate Radical Addition to β‐Acyloxy Acrylate Acceptors: An Approach to Acetate Aldol‐Type Products
Author(s) -
Sibi Mukund P.,
Zimmerman Jake,
Rheault Tara
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352096
Subject(s) - enantioselective synthesis , aldol reaction , chemistry , conjugate , nucleophile , addition reaction , substrate (aquarium) , nucleophilic addition , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , oceanography , mathematics , geology
An unusual bond‐construction strategy based on conjugate radical additions leads to acetate aldol‐like products with high enantioselectivity (see scheme). Unlike their ionic counterparts, the enantioselective nucleophilic radical addition to β‐acyloxyenoates proceeds without elimination and occurs by an Si ‐face radical addition to an s‐ cis conformer of the substrate (as shown).