Selenocyclisations of homoallylic sulfonamides: stereoselective methods for the elaboration of substituted pyrrolidines, pyrrolines and derivatives

Jones, Andrew D., Redfern, Adele L., Knight, David William, Morgan, Ian Rhys ORCID: https://orcid.org/0000-0002-0253-1855 and Williams, Andrew C. 2006. Selenocyclisations of homoallylic sulfonamides: stereoselective methods for the elaboration of substituted pyrrolidines, pyrrolines and derivatives. Tetrahedron 62 (39) , pp. 9247-9257. 10.1016/j.tet.2006.07.018

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Abstract

Selenocyclisations of the homoallylic sulfonamides [e.g., 26, 28 and 30] using phenylselanyl halides lead exclusively to β-selanyl-pyrrolidines [e.g., 27, 29 and 31] by an overall 5-endo-trig pathway, but with considerable variations in the stereochemical outcome, depending upon the substituents and the precise conditions used. Subsequent oxidative eliminations lead smoothly to the corresponding 3-pyrrolines and thence to poly-hydroxylated pyrrolidines.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Elsevier
ISSN:	0040-4020
Last Modified:	06 May 2023 01:30
URI:	https://orca.cardiff.ac.uk/id/eprint/58131

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