Inverse demand [4+ 2] cycloaddition reactions of allenamides: reactivity scopes of an electron deficient variant of allenamines

LL Wei, H Xiong, CJ Douglas, RP Hsung

Index: Wei, Lin-Li; Xiong, Hui; Douglas, Christopher J.; Hsung, Richard P. Tetrahedron Letters, 1999 , vol. 40, # 38 p. 6903 - 6907

Full Text: HTML

Citation Number: 57

Abstract

The synthesis and reactivity of a series of new allenamides are described. These electron deficient variants of allenamines are more stable than allenamines but possess comparable reactivity. Particularly, oxazolidinone and imidazolidinone substituted allenamides undergo efficient inverse demand [4+ 2] cycloaddition reactions with heterodienes, leading to unique pyranyl heterocycles. The reactivity differences between various allenamides containing ...