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Lewis Base Activation of Silyl Acetals: Iridium-Catalyzed Reductive Horner-Wadsworth-Emmons Olefination

Udaya Sree Dakarapu, Apparao Bokka, Parham Asgari, Gabriela Trog, Yuanda Hua, Hiep H. Nguyen, Nawal Rahman and Junha Jeon*

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

U. S. Dakarapu, A. Bokka, P. Asgari, G. Trog, Y. Hua, H. H. Nguyen, N. Rahman, J. Jeon, Org. Lett., 2015, 17, 5792-5795.

DOI: 10.1021/acs.orglett.5b02901 (free Supporting Information)



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Abstract

In an operationally convenient, mechanistically unique protocol, Lewis base activation of silyl acetals generates putative pentacoordinate silicate acetals, which fragment into aldehydes, silanes, and alkoxides in situ. Subsequent deprotonative metalation of phosphonate esters followed by HWE with aldehydes furnishes enoates.

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Key Words

unsaturated esters, Wittig-Horner reaction, silanes


ID: J54-Y2015