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
Publication
, Journal Article
Jump, JM; McPhail, AT; Cook, CE
Published in: Tetrahedron Letters
May 26, 1997
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.
Duke Scholars
Published In
Tetrahedron Letters
DOI
ISSN
0040-4039
Publication Date
May 26, 1997
Volume
38
Issue
21
Start / End Page
3691 / 3694
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
APA
Chicago
ICMJE
MLA
NLM
Jump, J. M., McPhail, A. T., & Cook, C. E. (1997). 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. Tetrahedron Letters, 38(21), 3691–3694. https://doi.org/10.1016/S0040-4039(97)00714-4
Jump, J. M., A. T. McPhail, and C. E. Cook. “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.” Tetrahedron Letters 38, no. 21 (May 26, 1997): 3691–94. https://doi.org/10.1016/S0040-4039(97)00714-4.
Jump JM, McPhail AT, Cook CE. 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. Tetrahedron Letters. 1997 May 26;38(21):3691–4.
Jump, J. M., et al. “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.” Tetrahedron Letters, vol. 38, no. 21, May 1997, pp. 3691–94. Scopus, doi:10.1016/S0040-4039(97)00714-4.
Jump JM, McPhail AT, Cook CE. 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. Tetrahedron Letters. 1997 May 26;38(21):3691–3694.
Published In
Tetrahedron Letters
DOI
ISSN
0040-4039
Publication Date
May 26, 1997
Volume
38
Issue
21
Start / End Page
3691 / 3694
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry