Stereoselectivity in the Photoinduced Electron Transfer (PET) promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: Rapid construction of 1-azabicyclo[m.n.0] alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine

DOI: 10.1039/P19960000219

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Journal of the Chemical Society. Perkin transactions I p. 219 - 224 (1996)

Update date:2022-08-03

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Authors:

Pandey, Ganesh

Reddy, Gottimukkula Devi

Chakrabarti, Debasish

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Article abstract of DOI:10.1039/P19960000219

PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stereoselective. The five-membered ring formation gives predominantly cis products while six-membered rings are trans. Application of such cyclisations to the synthesis of (±)-isoretronecanol 22a, (±)-epilupinine 29 and related alkaloids has been demonstrated. Copyright 1996 by the Royal Society of Chemistry.

Full text of DOI:10.1039/P19960000219

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