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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 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: 04 Jun 2017 06:17
URI: http://orca.cf.ac.uk/id/eprint/58131

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