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Synlett 1997; 12(12): 1375-1376
DOI: 10.1055/s-0032-1316827
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© Georg Thieme Verlag KG Stuttgart · New York

Dramatic Changeover of Regioselectivity in the Reduction of Propargylic Phosphates by Palladium(0)/SmI2/Proton Source System

Akihiro Yoshida
Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan, FAX 3 5734 2776; kmikami@o.cc.titech.ac.jp
,
Koichi Mikami
Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan, FAX 3 5734 2776; kmikami@o.cc.titech.ac.jp
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Publication Date:
22 November 2012 (online)

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Abstract

Regiodivergent synthesis of allenes and acetylenes was established in the reduction of propargylic phosphates. The palladium(0)-catalyzed reduction of secondary propargylic phosphates with samarium(II) iodide gave allenes or acetylenes by tuning proton sources (tert-butyl alcohol or dimethyl L-tartrate).