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Hydroxy‐ and Carboxy‐Substituted Allylsilanes: A Simple and Stereoselective Method of Preparation
Author(s) -
Moret Etienne,
Franzini Livia,
Schlosser Manfred
Publication year - 1997
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19971300306
Subject(s) - chemistry , metalation , butyllithium , reagent , stereoselectivity , silylation , hydrolysis , potassium , organic chemistry , medicinal chemistry , catalysis
When treated with two equivalents of a butyllithium/potassium tert ‐butoxide mixture, terminal olefins carrying unprotected hydroxy or carboxy groups generate allylmetal intermediates which can be trapped with chlorotrimethylsilane to afford functionalized (Z)‐2‐alkenyltrimethylsilanes. One equivalent of the superbasic reagent suffices if the unsaturated alcohols are first protected as acetals before being subjected to the metalation/silylation/hydrolysis sequence.