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Asymmetric Retro‐[1,4] Brook Rearrangement and Its Stereochemical Course at Silicon
Author(s) -
Nakazaki Atsuo,
Nakai Takeshi,
Tomooka Katsuhiko
Publication year - 2006
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.200503734
Subject(s) - stereocenter , silylation , electrophile , chemistry , group (periodic table) , stereochemistry , course (navigation) , enantioselective synthesis , organic chemistry , catalysis , physics , astronomy
Taking the silyl group a step further : An unprecedented rearrangement in an anion derived from an allyloxysilane occurs by a [1,4] shift of the silyl group (see scheme). The asymmetric synthesis of enantiomerically enriched γ‐functionalized allylsilanes with Si stereocenters can be accomplished with this retro‐[1,4] Brook rearrangement. E=electrophile.