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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)2511-2512
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number21
DOIs
Publication statusPublished - 1994

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Lactams
Indenes
Naphthalenes
X ray crystallography
Carbon
Atoms
2-piperidone
ethylene dichloride
aluminum chloride

Cite this

Bahajaj, Abood A. ; Bailey, Patrick D. ; Moore, Madeleine H. ; Morgan, Keith M. ; Vernon, John M. / Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones. In: Journal of the Chemical Society, Chemical Communications. 1994 ; No. 21. pp. 2511-2512.
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Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones. / Bahajaj, Abood A.; Bailey, Patrick D.; Moore, Madeleine H.; Morgan, Keith M.; Vernon, John M.

In: Journal of the Chemical Society, Chemical Communications, No. 21, 1994, p. 2511-2512.

Research output: Contribution to journalArticle

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AU - Vernon, John M.

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