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Zinc-Mediated Chain Extension Reaction of 1,3-Diketones to 1,4-Diketones and Diastereoselective Synthesis of trans-1,2-Disubstituted Cyclopropanols
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Section:Abstract
A variety of 1,3-diketones can be efficiently converted into the corresponding 1,4-diketones and trans-1,2-disubstituted cyclopropanols by using organozinc species in one-pot reactions. It was found that 2.3 equiv of CF3CO2ZnCH2I was effective to give the corresponding chain-extended products in 44−85% yields, while a mixture of organozinc species formed from 4.0 equiv of Et2Zn, 2.0 equiv of CF3CO2H, and 4.0 equiv of CH2I2 resulted in the formation of trans-1,2-disubstituted cyclopropanols with quite good yields and diastereoselectivity.
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
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- Published In Issue January 06, 2006
- Received September 16, 2005
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