The synthesis of azabicyclo[4.2.1]nonenes by the addition of a cyclopropenone to 4-vinyl substituted 1-azetines - Isomers of the homotropane nucleus

Karl Hemming, Paul A. O'Gorman, Michael I. Page

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The conversion of 4-vinyl substituted β-lactams into 4-vinyl substituted 1-azetines and their subsequent reaction with diphenylcyclopropenone (DPP) results in the formation of a highly functionalised 7-azabicyclo[4.2.1] nonene. This heterocyclic system is an isomer of the homotropane (9-azabicyclo[4.2.1]nonene) nucleus, which is the core structure of a class of alkaloid natural products that includes anatoxin-a. The key processes involved are two ring expansions, one of which constitutes a formal [3+2] cycloaddition and the other of which is an unusual aza-Cope (amino-Claisen) [3,3]-sigmatropic rearrangement.

LanguageEnglish
Pages425-428
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number4
Early online date2 Dec 2005
DOIs
Publication statusPublished - 23 Jan 2006

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Azetines
Cycloaddition
Cycloaddition Reaction
beta-Lactams
Biological Products
Alkaloids
Isomers
diphenylcyclopropenone
cyclopropenone
anatoxin a

Cite this

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The synthesis of azabicyclo[4.2.1]nonenes by the addition of a cyclopropenone to 4-vinyl substituted 1-azetines - Isomers of the homotropane nucleus. / Hemming, Karl; O'Gorman, Paul A.; Page, Michael I.

In: Tetrahedron Letters, Vol. 47, No. 4, 23.01.2006, p. 425-428.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The synthesis of azabicyclo[4.2.1]nonenes by the addition of a cyclopropenone to 4-vinyl substituted 1-azetines - Isomers of the homotropane nucleus

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KW - 1-Azetine

KW - Aza-Cope

KW - Cyclopropenone

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