A highly selective and practical method for enantiopure sulfoxides utilizing activated and functionally differentiated N-sulfonyl-1,2,3-oxathiazolidine-2-oxide derivatives

Angewandte Chemie - International Edition

Volumn 42, Issue 18, 2003, Pages 2032-2035

  Han, Zhengxu ^a   Krishnamurthy, Dhileepkumar ^a,b   Grover, Paul ^a   Wilkinson, H Scott ^a   Fang, Q Kevin ^a   Su, Xiping ^a   Lu, Zhi Hui ^a,b   Magiera, Daniel ^a   Senanayake, Chris H ^a,b  

^a SUNOVION PHARMACEUTICALS INC   (United States)

^b BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Chirality; Sulfoxides

Indexed keywords

MIXTURES; OXIDES; REACTION KINETICS;

STEREOSELECTIVITY;

SULFUR;

N SULFONYL 1,2,3 OXATHIAZOLIDINE 2 OXIDE DERIVATIVE; NOREPHEDRINE; SULFOXIDE; THIAZOLIDINE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038587682     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250644     Document Type: Article

References (33)

1. a) K. K. Andersen, Tetrahedron Lett. 1962, 93;
2. b) F. Wudl, T. B. K. Lee, J. Am. Chem. Soc. 1973, 95, 6349;
3. c) M. R. Barbachyn, C. R. Johnson in Asymmetric Synthesis, Vol. 4 (Eds.: J. D. Morrison, J. W. Scott), Acadamic Press, New York, 1983, p. 227;
4. d) O. Samuel, F. Rebiere, H. B. Kagan, J. Org. Chem. 1991, 56, 5991;
5. e) D. A. Evans, M. M. Faul, L. Colombo, J. J. Bisaha, J. Clardy, D. Cherry, J. Am. Chem. Soc. 1992, 114, 5977;
6. f) D. A. Cogan, G. Liu, K. Kim, B. J. Backes, J. A. Ellman, J. Am. Chem. Soc. 1998, 120, 8011, and references therein;
7. g) M. A. M. Capozzi, C. Cardellicchio, G. Fracchiolla, F. Naso, P. Tortorella, J. Am. Chem. Soc. 1999, 121, 4708;
8. h) N. Khiar, I. Fernandez, A. Alcudia in Advances in Sulfur Chemistry, Vol. 2 (Ed.: C. M. Rayner), JAJ, Stamford, 2000, chap. 3;
9. i) M. A. M. Capozzi, C. Cardellicchio, F. Naso, G. Spina, P. Tortorella, J. Org. Chem. 2001, 66, 5933-5936;
10. j) E. N. Prilezhaeva, Russ. Chem. Rev. 2000, 69, 367;
11. k) H. B. Kagan, P. Diter, Organosulfur Chem. 1998, 2, 1-39.
12. a) M. Matsugi, N. Fukuda, Y. Muguruma, T. Yamaguchi, J. Minamikawa,S. Otsuka, Tetrahedron 2001, 57, 2739-2744;
13. b) H. Cotton, T. Elebring, M. Larsson, L. Li, H. Sorensen, S. Unge, Tetrahedron: Asymmetry 2000, 11, 3819-3825.
14. H. B. Kagan in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, chap. 6c.
15. a) P. Metzner, A. Thuillier in Sulfur Reagents in Organic Synthesis, Academic Press, London, UK, 1994, chap. 2.6.2;
16. b) H. B. Kagan, F. Rebiere, Synlett 1990, 643-650.
17. a) S. C. Benson, J. K. Snyder, Tetrahedron Lett. 1991, 32, 5885-5888;
18. b) W. Oppolzer, O. Froelich, C. Wiaux-Zamar, G. Bernar-dinell, Tetrahedron Lett. 1997, 38, 2825-2828;
19. c) J. K. Whitesell, M.S. Wong, J. Org. Chem. 1991, 56, 4552-4554;
20. d) J. K. Whitesell, M. S. Wong, J. Org. Chem. 1994, 59, 597-601;
21. e) I. Fernandez, N. Khiar, J. M. Llera, F. Alcudia, J. Org. Chem. 1992, 57, 6789-6796;
22. f) H. El Ouazzani, N. Khiar, I. Fernandez, F. Alcudia, J. Org. Chem. 1997, 62, 287-291;
23. g) I. Fernandez, C. S. Araujo, M. J. Romero, F. Alcudia, N. Khiar, Tetrahedron 2000, 56, 3749-3753;
24. h) N. Khiar, C. S. Araujo, F. Alcudia, I. Fernandez, J. Org. Chem. 2002, 67, 345-356;
25. i) J. Posakony, J. T. Tewson, Synthesis 2002, 859.
26. Z. Han, D. Krishnamurthy, P. Grover, Q. K. Fang, C. H. Senanayake, J. Am. Chem. Soc. 2002, 124, 7880-7881.
27. a) The absolute stereochemistry of endo-3 and exo-3 was unambiguously established by single crystal X-ray analysis;
28. b) For the detailed experimental procedure, see Supporting Information;
29. c) As in the case of aminoindanol series, exo isomer of PMTOO can be obtained in 90% yield (with exo:endo = 9:1) using 2,6-di-tert-butylpyridine as a base.
30. Absolute configuration was deduced from the synthetic Scheme 3, involving two consecutive inversions of configuration and X-ray analysis of (R,S,R)-4b.
31. Use of tert-butyl (p-tolylsulfinyl) acetate in asymmetric synthesis, see G. Solladic, C. Bauder, E. Arce-Dubois, P. Y. Jacope, Tetrahedron Lett. 2001, 42, 2923-2925.
32. a) Polymer bound aryl N-sulfonyl 1,2,3-oxathiazolidine-2-oxide derivatives are under investigation;
33. b) The application of PMTOO 6 in the synthesis of valuable sulfinamides and polymer-supported sulfinamides are under investigation.