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

Lin Li Wei, Hui Xiong, Christopher J. Douglas, Richard P. Hsung

Research output: Contribution to journalArticlepeer-review

61 Scopus citations

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 different substitution patterns around the nitrogen atom are illustrated.

Original languageEnglish (US)
Pages (from-to)6903-6907
Number of pages5
JournalTetrahedron Letters
Volume40
Issue number38
DOIs
StatePublished - Sep 17 1999

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