Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones

Abood A. Bahajaj; Patrick D. Bailey; Madeleine H. Moore; Keith M. Morgan; John M. Vernon

doi:10.1039/C39940002511

Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones

Abood A. Bahajaj, Patrick D. Bailey, Madeleine H. Moore, Keith M. Morgan, John M. Vernon

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

Bicyclic lactams 14-17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.

Original language	English
Pages (from-to)	2511-2512
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	21
DOIs	https://doi.org/10.1039/C39940002511
Publication status	Published - 1994

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abstract = "Bicyclic lactams 14-17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.",

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AU - Morgan, Keith M.

AU - Vernon, John M.

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AB - Bicyclic lactams 14-17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.

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Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones

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