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- Title
Base-Mediated Cyclization of 3-[2-(2-Oxo-2-phenylethyl)-1-pyrrolidinyl]propanenitrile to 7-Phenyl-1,2,3,7,8,8a-hexahydroindolizine- 6-carbonitrile: What Lies Between?
- Authors
Morgans, Garreth L.; Fernandes, Manuel A.; van Otterlo, Willem A. L.; Michael, Joseph P.
- Abstract
Three intermediates along the reaction path by which 3-[2-(2-oxo-2-phenylethyl)-1-pyrrolidinyl]propanenitrile is converted into the rel-(7R,8aR)- and (7R,8aS)-diastereoisomers of 7-phenyl-1,2,3,7,8,8a-hexahydroindolizine-6-carbonitrile upon treatment with potassium tert-butoxide were isolated and characterized. They include the rel-(6R,7R,8aR)- and (6R,7S,8aS)-diastereoisomers of 7-hydroxy-7-phenyloctahydroindolizine-6-carbonitrile (the former obtained as a monohydrate), and 7-phenyl-1,2,3,5,8,8a-hexahydroindolizine-6-carbonitrile. The alcohol intermediates and the final products were also characterized by X-ray crystallography.
- Subjects
RING formation (Chemistry); INDOLIZIDINES synthesis; ALKALOID synthesis; CHEMOSELECTIVITY; AROMATIC compounds
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 16, p1902
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201701714