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Metal-Free, Regio- and Stereoselective Synthesis of Linear (E)-Allylic Compounds Using C, N, O, and S Nucleophiles

Xiaojun Huang, Brandon Fulton, Kana White and Alejandro Bugarin*

*Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, Texas 76019, United States, Email: bugarinuta.edu

X. Huang, B. Fulton, K. White, A. Bugarin, Org. Lett., 2015, 17, 2594-2597.

DOI: 10.1021/acs.orglett.5b00862 (free Supporting Information)


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Abstract

An efficient two-step protocol that employs readily available terminal alkenes as starting materials enables a highly regio- and stereoselective synthesis of various allylic acetates. This method affords linear (E)-isomers and tolerates several functional groups including halogen-containing molecules. For other weak oxygen, carbon, nitrogen, and sulfur nucleophiles, adducts were obtained in very good yields too.

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Key Words

1,2-dibromides, esters


ID: J54-Y2015