Asymmetric Synthesis of Bicyclic Amidines via Rhodium-Catalyzed [2+2+2] Cycloaddition of Carbodiimides

Asymmetric Synthesis of Bicyclic Amidines via Rhodium-Catalyzed [2+2+2] Cycloaddition of Carbodiimides

A highly enantioselective rhodium-catalyzed [2+2+2] cycloaddition of terminal alkynes and alkenyl carbodiimides has been developed. This reaction demonstrates the feasibility of olefin insertion into carbodiimide-derived metalacycles and provides a new class of chiral bicyclic amidines as the major...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 130; no. 11; pp. 3262 - 3263
Main Authors: Yu, Robert T, Rovis, Tomislav
Format: Journal Article
Language:English
Published: United States American Chemical Society 19-03-2008
Subjects:
Alkynes - chemistry
Amidines - chemical synthesis
Amidines - chemistry
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Carbodiimides - chemistry
Catalysis
Cyclization
Ligands
Molecular Structure
Rhodium - chemistry
Stereoisomerism
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Summary:A highly enantioselective rhodium-catalyzed [2+2+2] cycloaddition of terminal alkynes and alkenyl carbodiimides has been developed. This reaction demonstrates the feasibility of olefin insertion into carbodiimide-derived metalacycles and provides a new class of chiral bicyclic amidines as the major products. An isonitrile migration process responsible for the formation of the minor cycloadduct can be observed and is highly sensitive to the electronics of alkynyl substrates.
Bibliography:istex:E62448312DA63AF6E86432F6AAC0AC843ED05D1C
ark:/67375/TPS-GFWP4FW8-F
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja710065h