An isomünchnone-based method for the synthesis of highly substituted 2 (1 H)-pyridones

A Padwa, SM Sheehan, CS Straub

Index: Padwa, Albert; Sheehan, Scott M.; Straub, Christopher S. Journal of Organic Chemistry, 1999 , vol. 64, # 23 p. 8648 - 8659

Full Text: HTML

Citation Number: 120

Abstract

1-(Benzenesulfonyl-diazoacetyl)-pyrrolidin-2-one was prepared by a diazo transfer of 1-( benzenesulfonylacetyl)-pyrrolidin-2-one with p-acetamidobenzenesulfonyl azide and triethylamine. Treatment of the diazoimide with a catalytic quantity of rhodium (II) acetate resulted in the formation of an isomünchnone dipole, which underwent bimolecular trapping with various dipolarophiles in high yield. The initially formed cycloadducts were not ...