Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions

S.R. Yong, M.C. Williams, S.G. Pyne, A.T. Ung, Brian Skelton, Allan White, P. Turner

Research output: Contribution to journalArticle

66 Citations (Scopus)

Abstract

The phosphine-catalyzed [3 + 2]-cycloaddition of the 2-methylene gamma-lactams 4 and 5 and the acrylate 6 with the ylides derived from the ethyl ester, the amide or the chiral camphor sultam derivative of 2-butynoic acid (7a-c) give directly, or indirectly after reductive cyclization, spiro-heterocyclic products. The acid 32 underwent Curtius rearrangement and then acid hydrolysis to give two novel spirocyclic ketones, 41 and 42. (c) 2005 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)8120-8129
JournalTetrahedron
Volume61
DOIs
Publication statusPublished - 2005

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