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

Yong, SR; Williams, MC; Pyne, SG; Ung, AT; Skelton, BW; White, AH; Turner, P

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

Yong, SR Williams, MC Pyne, SG Ung, AT

Skelton, BW White, AH Turner, P

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Publication Type:: Journal Article
Citation:: Tetrahedron, 2005, 61 (34), pp. 8120 - 8129
Issue Date:: 2005-08-22

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Field	Value	Language
dc.contributor.author	Yong, SR	en_US
dc.contributor.author	Williams, MC	en_US
dc.contributor.author	Pyne, SG	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Skelton, BW	en_US
dc.contributor.author	White, AH	en_US
dc.contributor.author	Turner, P	en_US
dc.date.issued	2005-08-22	en_US
dc.identifier.citation	Tetrahedron, 2005, 61 (34), pp. 8120 - 8129	en_US
dc.identifier.issn	0040-4020	en_US
dc.identifier.uri	http://hdl.handle.net/10453/8494
dc.description.abstract	The phosphine-catalyzed [3+2]-cycloaddition of the 2-methylene γ-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 spiro-cyclic ketones, 41 and 42. © 2005 Elsevier Ltd. All rights reserved.	en_US
dc.relation.ispartof	Tetrahedron	en_US
dc.relation.isbasedon	10.1016/j.tet.2005.06.050	en_US
dc.subject.classification	Organic Chemistry	en_US
dc.title	Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions	en_US
dc.type	Journal Article
utslib.citation.volume	34	en_US
utslib.citation.volume	61	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	0304 Medicinal and Biomolecular Chemistry	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	34	en_US
pubs.publication-status	Published	en_US
pubs.volume	61	en_US

Abstract:

The phosphine-catalyzed [3+2]-cycloaddition of the 2-methylene γ-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 spiro-cyclic ketones, 41 and 42. © 2005 Elsevier Ltd. All rights reserved.

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http://hdl.handle.net/10453/8494