Synthesis of Optically Active Boron-Silicon Bifunctional Cyclopropane Derivatives through Enantioselective Copper(I)-Catalyzed Reaction of Allylic Carbonates with a Diboron Derivative

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 sil...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-09, Vol.47 (39), p.7424-7427
Main Authors: Ito, Hajime, Kosaka, Yuki, Nonoyama, Kousuke, Sasaki, Yusuke, Sawamura, Masaya
Format: Article
Language:English
Subjects:
asymmetric catalysis
boron
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Carbonates - chemistry
Catalysis
copper
Copper - chemistry
cyclization
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Models, Molecular
Molecular Structure
silicon
Silicon - chemistry
Stereoisomerism
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Summary: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 CC double bond.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802342