A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®

Journal Article

A convenient synthesis of novel 2,2,4-trisubstituted pyrrolidines via stereoselective 5-exo iodocyclization of the 2,2-disubstituted olefins 8 and 9 is described. Single crystal X-ray analysis of the oxazolidinone 15 confirmed the relative stereochemistry in this cyclization. As observed earlier in the formation of 2,2,4-trisubstituted tetrahydrofurans, the presence of a bulky aryl substituent on the olefin appears to direct the stereochemical outcome of these halocyclizations. © 2003 Elsevier Ltd. All rights reserved.

Full Text

Duke Authors

Cited Authors

  • McCormick, JL; Osterman, R; Chan, TM; Das, PR; Pramanik, BN; Ganguly, AK; Girijavallabhan, VM; McPhail, AT; Saksena, AK

Published Date

  • October 20, 2003

Published In

Volume / Issue

  • 44 / 43

Start / End Page

  • 7997 - 8000

International Standard Serial Number (ISSN)

  • 0040-4039

Digital Object Identifier (DOI)

  • 10.1016/j.tetlet.2003.08.114

Citation Source

  • Scopus