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

doi:10.1016/j.tet.2005.06.050

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 journal › Article › peer-review

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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 language	English
Pages (from-to)	8120-8129
Journal	Tetrahedron
Volume	61
DOIs	https://doi.org/10.1016/j.tet.2005.06.050
Publication status	Published - 2005

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

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.",

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

year = "2005",

doi = "10.1016/j.tet.2005.06.050",

language = "English",

volume = "61",

pages = "8120--8129",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Pergamon",

}

TY - JOUR

T1 - Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions

AU - Yong, S.R.

AU - Williams, M.C.

AU - Pyne, S.G.

AU - Ung, A.T.

AU - Skelton, Brian

AU - White, Allan

AU - Turner, P.

PY - 2005

Y1 - 2005

N2 - 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.

AB - 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.

U2 - 10.1016/j.tet.2005.06.050

DO - 10.1016/j.tet.2005.06.050

M3 - Article

SN - 0040-4020

VL - 61

SP - 8120

EP - 8129

JO - Tetrahedron

JF - Tetrahedron

ER -

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

Abstract

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