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

Ganesh Pandey; Gottimukkula Devi Reddy; Debasish Chakrabarti

doi:10.1039/P19960000219

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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

Ganesh Pandey, Gottimukkula Devi Reddy and Debasish Chakrabarti

Abstract

PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a–d to 1-azabicyclo[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.

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DOI: https://doi.org/10.1039/P19960000219
Article type: Paper

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J. Chem. Soc., Perkin Trans. 1, 1996, 219-224

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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

G. Pandey, G. D. Reddy and D. Chakrabarti, J. Chem. Soc., Perkin Trans. 1, 1996, 219 DOI: 10.1039/P19960000219

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Journal of the Chemical Society, Perkin Transactions 1

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

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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

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