Organozinc Reagents in DMSO Solvent: Remarkable Promotion of SN2′ Reaction for Allene Synthesis

Koji Kobayashi, Hiroshi Naka, Andrew E. H. Wheatley and Yoshinori Kondo*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza Aoba 6-3, Aoba-ku, Sendai 980-8578, Japan, Email: ykondomail.pharm.tohoku.ac.jp

K. Kobayashi, H. Naka, A. E. H. Wheatley, Y. Kondo, Org. Lett., 2008, 10, 3375-3377.

DOI: 10.1021/ol801249w (free Supporting Information)

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Abstract

The S_N2′ reaction of propragyl mesylates with organozinc reagents was dramatically improved in DMSO as solvent, and the conversion of a chiral substrate was successfully achieved without loss of optical purity using a LiCl-free diorganozinc reagent.

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Key Words

Allenes

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ID: J54-Y2008-2170