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( E )‐ and ( Z )‐β‐Borylallylsilanes by Alkyne Silaboration Followed by Regio‐ and Stereoselective Double‐Bond Migration
Author(s) -
Ohmura Toshimichi,
Oshima Kazuyuki,
Suginome Michinori
Publication year - 2011
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.201106077
Subject(s) - regioselectivity , double bond , stereoselectivity , alkyne , terminal (telecommunication) , bond , stereochemistry , chemistry , computer science , organic chemistry , catalysis , business , telecommunications , finance
Double take : β‐Borylallylsilanes have been synthesized by the regioselective silaboration of terminal alkynes followed by palladium‐catalyzed double‐bond migration of the resulting β‐borylalkenylsilanes (see scheme). The stereoselectivity of the double‐bond migration can be controlled by additives, thus leading to the stereocomplementary synthesis of ( E )‐ and ( Z )‐β‐borylallylsilanes.