Asymmetric Retro‐[1,4] Brook Rearrangement and Its Stereochemical Course at Silicon | Zendy

Nakazaki Atsuo | Zendy; Nakai Takeshi | Zendy; Tomooka Katsuhiko | Zendy

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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.

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