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
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