Synthesis of chiral ortho-thio-substituted phenyl phosphonodiamidates via a P-S to P-C rearrangement

Tetrahedron Letters

Volumn 45, Issue 20, 2004, Pages 3855-3859

  Mauger, Christelle ^a   Vazeux, Michel ^a   Masson, Serge ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

1,3 Sigmatropy; ortho Lithiation; Phosphonodiamidate; Phosphorodiamidothioate; Sulfoxide; Thiol

Indexed keywords

ALKYLATING AGENT; BENZENE DERIVATIVE; CARBON; DIAMINE DERIVATIVE; ETOMIDATE; LEWIS ACID; PHOSPHONIUM DERIVATIVE; SULFANILAMIDE DERIVATIVE; SULFUR DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHIRALITY; DERIVATIZATION; ENANTIOSELECTIVITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 1942504367     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.132     Document Type: Article

References (31)

1. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vols. 1-3:1999;Springer, Berlin.
2. Brunel J.M., Buono G. Majoral J.P. New Chiral Organophosphorus Catalysts in Asymmetric Synthesis, Topics in Current Chemistry. Vol. 220:2002;79-105 Springer, Berlin, Heidelberg.
3. Molt O., Schrader T. Synthesis. 18:2002;2633-2670.
4. Melvin L.S. Tetrahedron Lett. 22:1981;3375-3376.
5. Dhawan B., Redmore D. J. Org. Chem. 49:1984;4018-4021.
6. Dhawan B., Redmore D. Synth. Commun. 15:1985;411-416.
7. Dhawan B., Redmore D. Phosphorus Sulfur Silicon. 42:1989;177-182.
8. Jardine A.M., Vather S.M., Modro T.A. J. Org. Chem. 53:1988;3983-3985.
9. He Z., Modro T.A. Synthesis. 4:2000;565-570.
10. Moulin D., Bago S., Bauduin C., Darcel C., Jugé S. Tetrahedron: Asymmetry. 11:2000;3939-3956.
11. Legrand O., Brunel J.M., Buono G. Chem. Eur. J. 4:1998;1061-1105.
12. Brunel J.M., Constantieux T., Legrand O., Buono G. Tetrahedron Lett. 39:1998;2961-2964.
13. Legrand O., Brunel J.M., Buono G. Tetrahedron Lett. 39:1998;9419-9422.
14. Brunel J.M., Buono G. Tetrahedron Lett. 41:2000;2105-2108.
15. Masson S., Saint-Clair J.F., Saquet M. Synthesis. 1993;485-486.
16. Masson S., Saint-Clair J.F., Saquet M. Tetrahedron Lett. 1994;3083-3084.
17. Masson S., Saint-Clair J.F., Dore A., Saquet M. Bull. Chem. Soc. Fr. 133:1996;951-964.
18. Watanabe M., Date M., Kawanishi K., Akiyoshi R., Furukawa S. J. Heterocycl. Chem. 28:1991;173-176.
19. Legrand O., Brunel J.M., Buono G. Tetrahedron. 56:2000;595-603.
20. Hiroi K., Suzuki Y., Abe I., Kawagishi R. Tetrahedron. 56:2000;4701-4710.
21. Alexakis A., Mutti S., Mangeney J. J. Org. Chem. 57:1992;1224-1237.
22. Bennani Y.L., Hanessian S. Tetrahedron. 52:1996;13837-13866.
23. 2OPS: calcd: C, 56.74; H, 7.14; N, 9.45; S, 10.82; found: C, 56.95; H, 7.10; N, 9.60; S, 10.58.
24. 2OPS: calcd: C, 58.04; H, 7.47; N, 9.02; found: C, 58.48; H, 7.70; N, 9.06.
25. 2OPS: calcd: C, 56.74; H, 7.14; N, 9.45; S, 10.82; found: C, 56.81; H, 7.16; N, 9.32; S, 10.96.
26. 2PS: calcd: C, 55.20; H, 7.10; N, 8.58; S, 9.82; found: C, 55.85; H, 7.27; N, 8.83; S, 9.36.
27. Kessler H., Rieker A., Rundel W. Chem. Commun. 1968;475-476.
28. Mauger C., Masson S., Vazeux M., Saint-Clair J.F., Midura W.H., Drabowicz J., Mikolajczyk M. Tetrahedron: Asymmetry. 12:2001;167-174.
29. 18 led us to a racemic mixture. Very probably, the strong acidic conditions needed to hydrolyse the phosphonamido group racemized the sulfoxyde function.
30. Sandrinelli F., Perrio S., Beslin P. J. Org. Chem. 62:1997;8626-8627.
31. Sandrinelli F., Perrio S., Averbuch-Pouchot M.T. Org. Lett. 4:2002;3619-3622.