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Highly Stereoselective Synthesis of Z ‐Homoallylic Alcohols by Kinetic Resolution of Racemic Secondary Allyl Boronates
Author(s) -
Incerti–Pradillos Celia A.,
Kabeshov Mikhail A.,
Malkov Andrei V.
Publication year - 2013
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.201300709
Subject(s) - kinetic resolution , stereoselectivity , chemistry , resolution (logic) , computer science , organic chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , programming language
α to Z : Racemic α‐chiral allyl boronates, which are readily synthesized from the respective primary allyl halides, undergo a highly efficient kinetic resolution in a face‐ and Z ‐selective allylation of aldehydes catalyzed by the chiral Brønsted acid ( R )‐TRIP (see scheme; Epin=tetraethylethylene glycol).