π-Facial diastereoselectivity in the Diels-Alder reactions of cis-cyclohexa-3, 5-diene-1, 2-diol and derivatives with N-phenylmaleimide

JR Gillard, DJ Burnell

Index: Gillard, James R.; Burnell, D. Jean Canadian Journal of Chemistry, 1992 , vol. 70, # 5 p. 1296 - 1307

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Citation Number: 26

Abstract

N-Phenylmaleimide undergoes Diels-Alder cycloaddition predominantly to the face of cis- cyclohexa-3, 5-diene-1, 2-diol (3) syn to the oxygen functions. Derivatization can be used to alter the π-facial diastereoselectivity in a synthetically useful manner. The best cases are the exclusive, high yield, production of the syn-addition product with the trimethylsilyl ether derivative (8), and the exo-benzylidine derivative (26) gave a 96: 4 anti/syn ratio of ...