Practical Approach to α- or γ-Heterosubstituted Enoic Acids

Julia L. Shamshina and Timothy S. Snowden*

*Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 34587-0336, Email: snowdenbama.ua.edu

J. L. Shamshina, T. S. Snowden, Org. Lett., 2006, 8, 5881-5884.

DOI: 10.1021/ol0625132 (free Supporting Information)

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Abstract

The reaction of alkenyl trichloromethyl carbinols with various nucleophiles under protic basic conditions reveals that mercaptans participate by α-substitution (S_N2), wheareas hydroxide prefers γ-substitution with stereoselective allylic transposition (S_N2'). Regioselectivity with alkoxides depends upon alkene substitution.

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proposed mechanism

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Key Words

Jocic Reaction, Carboxylic Acids, α-Hydroxy acids

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ID: J54-Y2006-3980