Practical Approach to - or -Heterosubstituted Enoic Acids

Org. Lett., 8 (25), 5881 -5884, 2006. 10.1021/ol0625132 S1523-7060(06)02513-2
Web Release Date: November 10, 2006

Practical Approach to - or -Heterosubstituted Enoic Acids

Julia L. Shamshina and Timothy S. Snowden*

Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 34587-0336

snowden@bama.ua.edu

Received October 11, 2006

Abstract:

The reaction of alkenyl trichloromethyl carbinols with various nucleophiles under protic basic conditions reveals that mercaptans participate by

-substitution (S_N2) of the intermediate alkenyl gem-dichloroepoxides. Conversely, hydroxide results in preferential

-substitution with stereoselective allylic transposition (S_N2'). Regioselectivity with alkoxides depends upon the level of alkene substitution.

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