Catalysis of benzoin condensation by conformationally-restricted chiral bicyclic thiazolium salts

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 2925-2928

  Dvorak, Curt A ^b   Rawal, Viresh H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIN; THIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTALLIZATION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN;

EID: 0032492979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00439-0     Document Type: Article

References (22)

1. 2. Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 296-300. (CA: 1951, 45, 5148e)
2. 2. Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 296-300. (CA: 1951, 45, 5148e)
3. 3. (a) Stetter, H. Angew. Chem. Int. Ed. Engl. 1976, 5, 639-647.
4. (b) For a discussion of recent developments on the use of stable carbenes for benzoin-type condensations see: Teles, J.H.; Melder, J. P.; Ebel, K.; Schneider, R.; Geher, E.; Harder, W.; Brode, S.; Enders, D.; Breuer, K.; Raabe, G. Helv. Chim. Acta. 1996, 79, 61-83.
5. 4. (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726.
6. (b) Undue attention has been given to the mechanism over the last few years, stimulated primarily by an improbable mechanism proposed by Lopez-Calahorra and coworkers. See: Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242, and references cited therein.
7. 5. Breslow, R.; McNelis, E. . J Am. Chem. Soc. 1959, 81, 3080-3082.
8. 6. (a) Yamashita, K.; Sasaki, S.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817-4820.
9. (b) Marti, J.; Castells, J.; Lopez-Calahorra, F. Tetrahedron Lett. 1993, 34, 521-524.
10. (c) Zhao, C.; Chen, S.; Wu, P.; Wen, Z., Acta. Chimia. Sinica. 1988, 46, 784-790 (CA: 1988, 110, 192696r ).
11. (c) Zhao, C.; Chen, S.; Wu, P.; Wen, Z., Acta. Chimia. Sinica. 1988, 46, 784-790 (CA: 1988, 110, 192696r ).
12. (d) Tagaki, W.; Tamura, Y.; Yano, Y. Bull. Chem. Soc. Jpn. 1980, 53, 478-480.
13. (e) Sheehan, J.C.; Hara, T. J. Org. Chem. 1974, 39, 1196-1199.
14. (f) Sheehan, J.C.; Hunneman, D.H. J. Am. Chem. Soc. 1966, 88, 3666-3667.
15. 7. While this work was being readied for publication, Knight and Leeper reported the only other conformationally restricted thiazolium salts. See, Knight, R.L.; Leeper, F.J. Tetrahedron Lett. 1997, 38, 3611-3614.
16. 8. Taken from the Ph. D. thesis of C. A. Dvorak, The University of Chicago, 1998. This work was presented at the American Chemical Society 30th Annual Great Lakes Regional Meeting, Loyola University of Chicago, Chicago, IL, 5/30/97.
17. 9. Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev, 1994, 94, 2483-2547 and references therein.
18. 10. (a) Kolb, H.C.; Sharpless, K.B. Tetrahedron 1992, 48, 10515-10530.
19. (b) 1% IPA/Hexanes; flow=1mL/min; Welko-S,S column (Regis).
20. 11. Caldwell, W.T.; Fox, S.M. J. Am. Chem. Soc. 1951, 73, 2935-2936.
21. 12. Johnson, D.A. J. Am. Chem. Soc. 1955, 77, 2336-2337.
22. 13. No racemization was observed as confirmed by reduction of the salts to the corresponding thiazolidines and HPLC analysis. (10%IPA/Hex, flow=1mL/min).