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Synthesis of Optically Active Boron–Silicon Bifunctional Cyclopropane Derivatives through Enantioselective Copper(I)‐Catalyzed Reaction of Allylic Carbonates with a Diboron Derivative
Author(s) -
Ito Hajime,
Kosaka Yuki,
oyama Kousuke,
Sasaki Yusuke,
Sawamura Masaya
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.200802342
Subject(s) - cyclopropane , bifunctional , allylic rearrangement , enantioselective synthesis , chemistry , silylation , ligand (biochemistry) , regioselectivity , boron , silicon , medicinal chemistry , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , ring (chemistry) , biochemistry , receptor
Two for the show : A copper(I)‐catalyzed reaction forms boron–silicon bifunctional cyclopropane derivatives from γ‐silylated allylic carbonates and a diboron species (see scheme). The reaction is highly enantioselective when a chiral bisphosphine ligand is used. The stereoelectronic effect of the silyl group induces unusual regioselectivity of the borylcopper(I) addition across the CC double bond.