Tetrahedron Letters p. 6473 - 6476 (1994)
Update date:2022-08-18
Topics:
Weidner-Wells, Michele A.
Fraga, Stephanie A.
Demers, James P.
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.
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