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Letter

Practical Approach to α- or γ-Heterosubstituted Enoic Acids

Supporting Info

Julia L. Shamshina and Timothy S. Snowden*

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

Org. Lett., 2006, 8 (25), pp 5881–5884

DOI: 10.1021/ol0625132

Publication Date (Web): November 10, 2006

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

, snowden@bama.ua.edu

Abstract

The reaction of alkenyl trichloromethyl carbinols with various nucleophiles under protic basic conditions reveals that mercaptans participate by α-substitution (S_N2) of the intermediate alkenyl gem-dichloroepoxides. Conversely, hydroxide results in preferential γ-substitution with stereoselective allylic transposition (S_N2‘). Regioselectivity with alkoxides depends upon the level of alkene substitution.

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Published In Issue December 07, 2006
Received October 11, 2006

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Letter

Practical Approach to α- or γ-Heterosubstituted Enoic Acids

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton

A Concise Total Synthesis of (−)-Quinocarcin via Aryne Annulation

Total Synthesis of (−)-2-epi-Peloruside A

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