Tetrahedron letters

Control of regioselectivity in nitrile oxide cycloadditions to cinnamic acid derivatives

MA Weidner-Wells, SA Fraga, JP Demers

Index: Weidner-Wells, Michele A.; Fraga, Stephanie A.; Demers, James P. Tetrahedron Letters, 1994 , vol. 35, # 35 p. 6473 - 6476

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Citation Number: 13

Abstract

Abstract Tertiary cinnamides undergo cycloaddition with benzonitrile oxides producing the 5- phenyl and 4-phenyl regioisomers 2b and 3b in a 25–30: 75–70 ratio. This result is opposite to that obtained utilizing methyl cinnamate 1a as the dipolarophile. A synthetically useful method for the preparation of the acid 3c, derived from what is usually the minor regioisomer, has been developed by taking advantage of this reversal of regiochemistry.