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Asymmetric Synthesis of Trisubstituted Allenes: Copper-Catalyzed Alkylation and Arylation of Propargylic Phosphates

Mycah R. Uehling, Samuel T. Marionni and Gojko Lalic*

*Department of Chemistry, University of Washington, Seattle, Washington 98195, United States, Email:

M. R. Uehling, S. T. Marionni, G. Lalic, Org. Lett., 2012, 14, 362-365.

DOI: 10.1021/ol2031119 (free Supporting Information)


Copper-catalyzed alkylation and arylation of chiral propargylic phosphates using alkyl boranes and arylboronic esters as organoboron nucleophiles enables the asymmetric synthesis of trisubstituted allenes with excellent chirality transfer and regioselectivity, together with good functional group compatibility.

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ID: J54-Y2012-0130