LDA-mediated selective addition reaction of vinylidenecyclopropanes with aldehydes, ketones, and enones: facile synthesis of vinylcyclopropenes, allenols, and 1,3-enynes.

Org Lett

State Key Laboratory of Organometallic Chenistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China 200032.

Published: May 2008

Highly selective addition reaction of vinylidenecyclopropanes 1 was realized by treatment with LDA in THF and quenching with aldehydes, ketones, and enones. A number of vinylcyclopropenes, allenols, and 1,3-enynes were obtained selectively in moderate to good yields depending on the nature of different electrophiles.

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http://dx.doi.org/10.1021/ol800463kDOI Listing

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