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Phosphorus(III)-Mediated Stereoconvergent Formal [4+1]-Cycloannulation of 1,2-Dicarbonyls and o-Quinone Methides: A Multicomponent Assembly of 2,3-Dihydrobenzofurans

Kevin X. Rodriguez, Justin D. Vail and Brandon L. Ashfeld*

*Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States, Email: bashfeldnd.edu

K. X. Rodriguez, J. D. Vail, B. L. Ashfeld, Org. Lett., 2016, 18, 4514-4517.

DOI: 10.1021/acs.orglett.6b02122


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Abstract

A phosphorus(III)-mediated formal [4+1]-cycloaddition of 1,2-dicarbonyls and o-quinone methides provides 2,3-dihydrobenzofurans. Subtle steric interactions involved in the [4+1]-cycloannulation have an impact on yield and stereoselectivity in dihydrobenzofuran formation.

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Key Words

2,3-Dihydrobenzofurans


ID: J54-Y2016