Preparation of (S)-4-Isopropyl-N-propanoyl-1,3-thiazolidine-2-thione

Organic Syntheses

Volumn 86, Issue , 2009, Pages 70-80

  Gálvez, Erik ^a   Romea, Pedro ^b   Urpí, Fèlix ^a,c   Jewett, John C ^d   Rawal, Viresh H ^e  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c HARVARD UNIVERSITY   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e University of California ^*

Author keywords

[No Author keywords available]

Indexed keywords

EID: 66149095556     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.1002/0471264229.os086.08     Document Type: Article

References (35)

1. Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391-2393.
2. Delaunay, D.; Toupet, L.; Le Corre, M. J. Org. Chem. 1995, 60, 6604-6607.
3. Juaristi, E.; Martínez-Richa, A.; García-Rivera, A.; Cruz-Sánchez, J. S. J. Org. Chem. 1983, 48, 2603-2606.
4. Occasionally, 1,3-thiazolidine-2-thiones are prepared from β-amino thiols, see: Zhang, Y.; Sammakia, T. Org. Lett. 2004, 6, 3139-3141.
5. For a review, see: Velázquez, F.; Olivo, H. F. Curr. Org. Chem. 2002, 6, 303-340.
6. a) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25.
7. b) Zhang, Y.; Sammakia, T. J. Org. Chem. 2006, 71, 6262-6265.
8. Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894-902.
9. Crimmins, M. T.; Shamszad, M. Org. Lett. 2007, 9, 149-152.
10. a) Yamada, S. J. Org. Chem. 1996, 61, 941-946. See also:
11. b) Nagao, Y.; Kawabata, K.; Seno, K.; Fujita, E. J. Chem. Soc., Perkin I 1980, 2470-2473.
12. c) Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 115-111.
13. d) Sun, Y.-P.; Wu, Y. Synlett 2005, 1477-1479.
14. Mixed anhydrides have also been used as acylating reagents, see: Wu, Y.; Shen, X.; Yang, Y.-Q.; Hu, Q.; Huang, J.-H. J. Org. Chem. 2004, 69, 3857-3865.
15. a) Nagao, Y.; Ikeda, T.; Yagi, M.; Fujita, E.; Shiro, M. J. Am. Chem. Soc. 1982, 104, 2079-2081.
16. b) Nagao, Y.; Miyasaka, T.; Seno, K.; Fujita, E.; Shibata, D.; Doi, E. J. Chem. Soc., Perkin Trans. 1 1984, 2439-2446.
17. c) Nagao, Y.; Nagase, Y.; Kumagai, T.; Matsunaga, H.; Abe, T.; Shimada, O.; Hayashi, T.; Inoue, Y. J. Org. Chem. 1992, 57, 4243-4249.
18. a) Andrade, C. K. Z.; Rocha, R. O.; Vercillo, O. E.; Silva, W. A.; Matos, R. A. F. Synlett 2003, 2351-2352.
19. b) Franck, X.; Langlois, E.; Outurquin, F. Synthesis 2007, 719-724.
20. González, A.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952.
21. Crimmins, M. T.; She, J. Synlett 2004, 1371-1374.
22. a) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc 2002, 124, 392-393.
23. b) Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127-1130.
24. For boron-mediated aldol reactions from chiral 1,3-thiazolidine-2- thiones, see: Hsiao, C-N.; Liu, L.; Miller, M. J. J. Org. Chem. 1987, 52, 2201-2206.
25. a) Nagao, Y.; Kumagai, T.; Tamai, S.; Abe, T.; Kuramoto, Y.; Taga, T.; Aoyagi, S.; Nagase, Y.; Ochiai, M.; Inoue, Y.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 4673-4675.
26. b) Barragán, E.; Olivo, H. F.; RomeroOrtega, M.; Sarduy, S. J. Org. Chem. 2005, 70, 4214-4217.
27. Ambhaikar, N. B.; Snyder, J. P.; Liotta, D. C. J. Am. Chem. Soc. 2003, 125, 3690-3691.
28. a) Cosp, A.; Romea, P.; Talavera, P.; Urpí, F.; Vilarrasa, J.; FontBardia, M.; Solans, X. Org. Lett. 2001, 3, 615-617.
29. b) Cosp, A.; Larrosa, I.; Vilasis, I.; Romea, P.; Urpí, F.; Vilarrasa, J. Synlett 2003, 1109-1112.
30. Larrosa, I.; Romea, P.; Urpí, F.; Balsells, D.; Vilarrasa, J.; Font-Bardia, M.; Solans, X. Org. Lett. 2002, 4, 4651-4654.
31. a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
32. b) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706-8707.
33. Evans, D. A.; Thomson, R. J. J. Am. Chem. Soc. 2005, 127, 10506-10507.
34. Evans, D. A.; Thomson, R. J.; Franco, F. J. Am. Chem. Soc. 2005, 127, 10816-10817.
35. Wu, Y.; Sun, Y.-P.; Yang, Y.-Q.; Hu, Q.; Zhang, Q. J. Org. Chem. 2004, 69, 6141-6144.