A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®
Publication
, Journal Article
McCormick, JL; Osterman, R; Chan, TM; Das, PR; Pramanik, BN; Ganguly, AK; Girijavallabhan, VM; McPhail, AT; Saksena, AK
Published in: Tetrahedron Letters
October 20, 2003
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.
Duke Scholars
Published In
Tetrahedron Letters
DOI
ISSN
0040-4039
Publication Date
October 20, 2003
Volume
44
Issue
43
Start / End Page
7997 / 8000
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
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McCormick, J. L., Osterman, R., Chan, T. M., Das, P. R., Pramanik, B. N., Ganguly, A. K., … Saksena, A. K. (2003). A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®. Tetrahedron Letters, 44(43), 7997–8000. https://doi.org/10.1016/j.tetlet.2003.08.114
McCormick, J. L., R. Osterman, T. M. Chan, P. R. Das, B. N. Pramanik, A. K. Ganguly, V. M. Girijavallabhan, A. T. McPhail, and A. K. Saksena. “A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®.” Tetrahedron Letters 44, no. 43 (October 20, 2003): 7997–8000. https://doi.org/10.1016/j.tetlet.2003.08.114.
McCormick JL, Osterman R, Chan TM, Das PR, Pramanik BN, Ganguly AK, et al. A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®. Tetrahedron Letters. 2003 Oct 20;44(43):7997–8000.
McCormick, J. L., et al. “A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®.” Tetrahedron Letters, vol. 44, no. 43, Oct. 2003, pp. 7997–8000. Scopus, doi:10.1016/j.tetlet.2003.08.114.
McCormick JL, Osterman R, Chan TM, Das PR, Pramanik BN, Ganguly AK, Girijavallabhan VM, McPhail AT, Saksena AK. A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®. Tetrahedron Letters. 2003 Oct 20;44(43):7997–8000.
Published In
Tetrahedron Letters
DOI
ISSN
0040-4039
Publication Date
October 20, 2003
Volume
44
Issue
43
Start / End Page
7997 / 8000
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