Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 7, Issue 10, Pages 2411-2418Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201200467
Keywords
alkynes; butyrolactones; carbon dioxide; hydrocarboxylation; nickel
Categories
Funding
- National Basic Research Program of China [2009CB825300]
- National Natural Science Foundation of China [20732005]
- Project for Basic Research in Natural Science Issued by Shanghai Municipal Committee of Science [08dj1400100]
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An efficient nickel(0)-catalyzed highly regio- and stereoselective hydrocarboxylation of homopropargylic alcohols with ZnEt2 in the presence of CO2 (1 atm, balloon) to synthesize a-alkylidene-?-butyrolactones is described. The catalyst is highly active and can be applied for the synthesis of (optically active) mono- or bicyclic a-alkylidene-?-butyrolactones with excellent regio- and stereoselectivity and good functional group tolerance. The potential of the reaction has been demonstrated in the first synthesis of (+/-)-heteroplexisolide E.
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