Catalytic diastereoselective imidation of diaryl sulfides bearing a chiral oxazolinyl moiety with chloramine T trihydrate

Angewandte Chemie - International Edition

Volumn 38, Issue 9, 1999, Pages 1288-1289

  Takada, Hiroya ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Chloramine T.; Imidations; Sulfimides

Indexed keywords

OXAZOLINE DERIVATIVE; SULFIDE; TOSYLCHLORAMIDE SODIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONFORMATION; ENANTIOMER; METHYLATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033519191     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990503)38:9<1288::AID-ANIE1288>3.0.CO;2-5     Document Type: Article

References (20)

1. a) H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, Chem. Commun. 1996, 931;
2. b) H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, C. P. Baird, T. J. Sparey, P. C. Taylor, J. Org. Chem. 1997, 62, 6512;
3. c) H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, Phosphorus Sulfur Silicon Relat. Elem. 1997, 120-121, 363.
4. Y. Miyake, H. Takada, K. Ohe, S. Uemura, J. Chem. Soc. Perkin Trans. 1 1998, 2373.
5. H. Takada, M. Oda, Y. Miyake, K. Ohe, S. Uemura, Chem. Commun. 1998, 1557.
6. Y. Yamada, T. Yamamoto, M. Okawara, Chem. Lett. 1975, 361.
7. a) J. F. Bower, C. J. Martin, D. J. Rawson, A. M. Z. Slawin, J. M. J. Williams, J. Chem. Soc. Perkin Trans. 1 1996, 333;
8. b) J. F. Bower, J. M. J. Williams, Tetrahedron Lett. 1994, 35, 7111.
9. a) J. V. Allen, J. F. Bower, J. M. J. Williams, Tetrahedron: Asymmetry 1994, 5, 1895;
10. b) J. M. J. Williams, Synlett 1996, 705.
11. Chloramine T trihydrate is commercially available and much cheaper than TsN=IPh.
12. [1]
13. a) J. Day, D. J. Cram J. Am. Chem. Soc. 1965, 87, 4398;
14. b) D. J. Cram, J. Day, D. R. Rayner, D. M. von Schriltz, D. J. Duchamp, D. C. Garwood, J. Am. Chem. Soc. 1970, 92, 7369.
15. K. Tsujihara, N. Furukawa, K. Oae, S. Oae, Bull. Chem. Soc. Jpn. 1969, 42, 2631.
16. Chloramine T is a powerful positive chlorine releasing reagent toward alkenes: B. Damin, J. Garapon, B. Sillion, Tetrahedron Lett. 1980, 21, 6985;
17. B. Damin, J. Garapon, B. Sillion, Tetrahedron Lett. 1981, 22, 362.
18. P. S. Aujla, C. P. Baird, P. C. Talyor, H. Mauger, Y. Vallée, Tetrahedron Lett. 1997, 38, 7453.
19. T. Yoshimura, T. Omata, N. Furukawa, S. Oae, J. Org. Chem. 1976, 41, 1728.
20. [6]