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General Approach to Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Alkylboranes

Hirohisa Ohmiya*, Umi Yokobori, Yusuke Makida and Masaya Sawamura*

*Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Email: ohmiyasci.hokudai.ac.jp, sawamurasci.hokudai.ac.jp

H. Ohmiya, U. Yokobori, Y. Makida, M. Sawmura, Org. Lett., 2011, 13, 6312-6315.

DOI: 10.1021/ol202866h (free Supporting Information)


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Abstract

Copper-catalyzed γ-selective coupling between propargylic phosphates and alkylboron compounds affords multisubstituted allenes with various functional groups. The reaction of enantioenriched propargylic phosphates to give axially chiral allenes proceeds with excellent chirality transfer with 1,3-anti stereochemistry.

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Key Words

allenes


ID: J54-Y2011-3540