Organoselenium-induced cyclization of 2-alkenylthiazolines to functionalized γ-lactams

Synlett

Volumn , Issue 6, 1999, Pages 733-734

  Terao, Keiji ^a   Kunishima, Munetaka ^b   Tani, Shohei ^b  

^a Wacker Chemicals East Asia Ltd   (Japan)

^b KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

Amidoselenation; Selenides; Thiazolines; Thiols; lactams

Indexed keywords

GAMMA LACTAM DERIVATIVE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033001929     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2728     Document Type: Article

References (12)

1. For example: Dowle, M. D.; Davis, D. J. Chem. Soc. Rev. 1979, 171.
2. Terao, K.; Toshimitsu, A.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 1986, 1837.
3. Toshimitsu, A.; Terao, K.; Uemura, S. J. Org. Chem. 1987, 52, 2018.
4. Knapp, S.; Levorse, A. T.; J. Org. Chem. 1988, 53, 4006.
5. Webb II, R. R.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 1357.
6. Kimpe, N. D.; Boelens, M. J. Chem. Soc., Chem. Commun. 1993, 916.
7. Takahata, H.; Wang, E. C.; Ikuro, K.; Yamazaki, T.; Momose, T. Heterocycles 1992, 34, 435.
8. Starting la was synthesized from 1-methyl-1,3-thiazoline by allylation with nBuLi/allyl bromide. Similarly, 1b and 1c were prepared from 1a (n-BuLi/benzyl bromide or n-BuLi/ iodomethane).
9. 1H NMR, IR, and MS).
10. The stereochemistries were not determined.
11. 1H NMR analysis of the resulting diastereoisomeric products indicates the formation of methylmercapto group.
12. 19NOSSe: 329.0352. Found:329.0336.