Reversal of expected stereochemical outcome in the oppolzer reaction of a cyclic N-enoylsultam: Enantioselective synthesis and absolute configuration of antispermatogenic hexahydroindeno[1,2-c]pyridines

Journal Article (Journal Article)

p-Tolylmagnesium bromide added with high enantioselectivity to a cyclic enoylsultam (4), but the diastereofacial selectivity (determined by X-ray crystallography of the product) was opposite that reported for acyclic enoylsultams. The reaction was used in an enantioselective synthesis of antispermatogenic hexahydroindenopyridines and allowed the absolute configuration of the active enantiomer (1) to be determined.

Full Text

Duke Authors

Cited Authors

  • Jump, JM; McPhail, AT; Cook, CE

Published Date

  • May 26, 1997

Published In

Volume / Issue

  • 38 / 21

Start / End Page

  • 3691 - 3694

International Standard Serial Number (ISSN)

  • 0040-4039

Digital Object Identifier (DOI)

  • 10.1016/S0040-4039(97)00714-4

Citation Source

  • Scopus