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Regioselective Aliphatic Retro‐[1,4]‐Brook Rearrangements
Author(s) -
Mori Yuji,
Futamura Yutaka,
Horisaki Kazumi
Publication year - 2008
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.200702539
Subject(s) - regioselectivity , silylation , selectivity , chemistry , stereochemistry , organic chemistry , catalysis
A turn‐up for the Brook : The relative ease of silyl migration in the aliphatic retro‐Brook rearrangements of α,γ‐disilyloxy organolithium compounds (see scheme) has been revealed for the first time to be [1,2]≪[1,4]. The increasing size of the silyloxy group at the γ position relative to that at the α position induces higher [1,4] selectivity.
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