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3,3,3-Trichloropropyl-1-triphenylphosphorane: A Reagent for the Synthesis of (Z)-1,3-Enynes, (Z,Z)-1-Chloro-1,3-dienes, and 1,3-Diynes^†

Supporting Info

Maheswaran S. Karatholuvhu and Philip L. Fuchs*

Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907

J. Am. Chem. Soc., 2004, 126 (44), pp 14314–14315

DOI: 10.1021/ja045112v

Publication Date (Web): October 13, 2004

†

Conjunctive reagents for the Chiral Carbon Catalog 2 (for 1, see: Li, X.; Lantrip, D.; Fuchs, P. L. J. Am. Chem. Soc. 2003, 125, 14262−14263).

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pfuchs@purdue.edu

Abstract

3,3,3-Trichloropropyl-1-triphenylphosphonium chloride is conveniently prepared from 2-chloroethanol, triphenylphosphine, and trichloroacetic acid. Deprotonation of this reagent generates 3,3,3-trichloropropyl-1-triphenylphosphorane, which reacts with aldehydes to give trichloromethylated (Z)-olefins, which are useful for the synthesis of (Z)-1,3-enynes, (Z,Z)-1-chloro-1,3-dienes, and 1,3-diynes in high yields and stereospecificities.

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