Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 33, Pages 9512-9516Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501918
Keywords
allenes; asymmetric catalysis; copper; diazo compounds; synthetic methods
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Funding
- National Natural Science Foundation of China [21222206, 21332003, 21321061]
- Fok Ying Tung Education Foundation [141115]
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The asymmetric CH insertion of -diazoesters into 1-alkynes was achieved using chiral cationic guanidinium salts and copper(I) complexes. Optically active 2,4-disubstituted allenoates were generated under mild reaction conditions from various -diazoesters and 1-alkynes in high yield (up to 99%) and enantioselectivity (up to 97:3 e.r.). Control experiments excluded the possibility of an asymmetric isomerization of alkynoates.
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