STEREOSELECTIVITY IN THE PHOTOINDUCED ELECTRON-TRANSFER (PET) PROMOTED INTRAMOLECULAR CYCLIZATIONS OF 1-ALKENYL-2-SILYL-PIPERIDINES AND 1-ALKENYL-2-SILYL-PYRROLIDINES - RAPID CONSTRUCTION OF 1-AZABICYCLO[M.N.O] ALKANES AND STEREOSELECTIVE SYNTHESIS OF (+ -)-ISORETRONECANOL AND (+/-)-EPILUPININE/

Authors
PANDEY G REDDY GD CHAKRABARTI D
Citation
G. Pandey et al., STEREOSELECTIVITY IN THE PHOTOINDUCED ELECTRON-TRANSFER (PET) PROMOTED INTRAMOLECULAR CYCLIZATIONS OF 1-ALKENYL-2-SILYL-PIPERIDINES AND 1-ALKENYL-2-SILYL-PYRROLIDINES - RAPID CONSTRUCTION OF 1-AZABICYCLO[M.N.O] ALKANES AND STEREOSELECTIVE SYNTHESIS OF (+ -)-ISORETRONECANOL AND (+/-)-EPILUPININE/, Journal of the Chemical Society. Perkin transactions. I, (2), 1996, pp. 219-224
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
2
Year of publication
1996
Pages
219 - 224
Database
ISI
SICI code
0300-922X(1996):2<219:SITPE(>2.0.ZU;2-G
Abstract
PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piper idines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stere oselective. The five-membered ring formation gives predominantly cis p roducts while six-membered rings are trans. Application of such cyclis ations to the synthesis of (+/-)-isoretronecanol 22a, (+/-)-epilupinin e 29 and related alkaloids has been demonstrated.