Direct synthesis of methyl 2-diazo-4-aryl-3-butenoates and their application to the enantioselective synthesis of 4-aryl-4-(1-naphthyl)-2-butenoates

Huw M.L Davies,Jaemoon Yang,James R Manning

doi:10.1016/j.tetasy.2006.01.023

Direct synthesis of methyl 2-diazo-4-aryl-3-butenoates and their application to the enantioselective synthesis of 4-aryl-4-(1-naphthyl)-2-butenoates

Huw M.L Davies, Jaemoon Yang + Show 1 more

https://doi.org/10.1016/j.tetasy.2006.01.023

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Journal: Tetrahedron: Asymmetry	Publication Date: Feb 1, 2006
Citations: 22

Affiliation: University at Buffalo, State University of New York

#Rearrangement Pathway #Catalyzed Reaction + Show 6 more

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Abstract

An improved one-flask synthesis of various methyl 2-diazo-4-aryl and 4-heteroaryl-3-butenoates, precursors to donor/acceptor substituted carbenoids, is described. Their Rh 2( S-DOSP) 4 catalyzed reaction with 1-acetoxy-3,4-dihydronaphthalene, via a combined C–H activation/Cope rearrangement pathway followed by elimination of acetic acid affords a highly enantioselective (98–99% ee) entry to methyl 4-aryl- and 4-heteroaryl-4-(1-naphthyl)-2-butenoates.

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