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Generation of Organolithium Compounds bearing Super Silyl Ester and their Application to Matteson Rearrangement
Author(s) -
Oda Susumu,
Yamamoto Hisashi
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.201304225
Subject(s) - silylation , moiety , electrophile , chemistry , aryl , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , alkyl
It's super‐silyl‐fragilithyl‐ester‐aryl‐docious : The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives α‐functionalization of the ester moiety by Matteson rearrangement.