Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 11, Pages 3262-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja710065h
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Funding
- NIGMS NIH HHS [R01 GM080442-01A1, R01 GM080442, GM080442] Funding Source: Medline
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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.
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