Generation of Organolithium Compounds bearing Super Silyl Ester and their Application to Matteson Rearrangement | Zendy

Oda Susumu | Zendy; Yamamoto Hisashi | Zendy

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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.

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