Stereoselective synthesis of α-hydroxy-β-amino acid derivatives from β-hydroxy-γ,δ-unsaturated sulfilimine

Tetrahedron Letters

Volumn 49, Issue 20, 2008, Pages 3216-3220

  Raghavan, Sadagopan ^a   Mustafa, Shaik ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

(2S,3R) AHDA; (2S,3R) AHPBA; Bromo carbamate; N Cbz sulfilimine; N Sulfinyl benzylcarbamate; Sulfoxide

Indexed keywords

ALKENE; ALPHA HYDROXY BETA AMINO ACID DERIVATIVE; AMINO ACID DERIVATIVE; BETA HYDROXY GAMMA DELTA UNSATURATED SULFILIMINE; BROMO CARBAMATE; CARBAMIC ACID DERIVATIVE; IMINE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 41949086696     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.114     Document Type: Article

References (40)

1. Nicolaou K.C., Dai W.-M., and Guy R.K. Angew. Chem., Int. Ed. Engl. 33 (1994) 15
2. Aoyagi T., Tobe H., Kojima F., Hamada M., Takeuchi T., and Umezawa H. J. Antibiot. 31 (1978) 636
3. Iizuka K., Kamijo T., Harada H., Akahane K., Kubota T., Umeyama H., and Kiso Y. Chem. Commun. (1989) 1678
4. Umemura E., Tsuchiya T., and Umezawa S. J. Antibiot. 41 (1988) 530
5. Sánchez-Obregon R., Salgado F., Ortiz B., Díaz E., Yuste F., Walls F., and García Ruano J.L. Tetrahedron 63 (2007) 10521 and references cited therein
6. Raghavan S., and Rasheed M.A. Tetrahedron: Asymmetry 14 (2003) 1371 and references cited therein
7. Raghavan S., Naveen Kumar Ch., Tony K.A., Ramakrishna Reddy S., and Ravi Kumar K. Tetrahedron Lett. 45 (2004) 7231
8. For the preparation of optically active sulfilimines from sulfoxides using N-sulfinyl-p-toluenesulfonamide see:. Yamgishi F.G., Rayner D.R., Zwicker E.T., and Cram D.J. J. Am. Chem. Soc. 95 (1973) 1916
9. Christensen B.W. J. Chem. Soc. D (1971) 597
10. Cram D.J., Day J., Rayner D.R., von Schriltz D.M., Duchamp D.J., and Garwood D.C. J. Am. Chem. Soc. 92 (1970) 7369
11. Christensen B.W., and Kjaer A. Chem. Commun. (1969) 934
12. Johnson C.R., and Rigau J.J. J. Org. Chem. 33 (1968) 4340
13. Using N,N′-bis(p-toluenesulfonyl)sulfur diimide see Ref. 7a.
14. Using p-tosyl isocyanate see:. Garwood D.C., Jones M.R., and Cram D.J. J. Am. Chem. Soc. 95 (1973) 1925
15. The β-hydroxy sulfoxides can be prepared readily from the keto sulfoxide by diastereoselective reduction following Solladie's protocol, see:. Solladie G., Demailly G., and Greck C. Tetrahedron Lett. 26 (1985) 435
16. Solladie G., Frechou C., Demailly G., and Greck C. J. Org. Chem. 51 (1986) 1912
17. Carreno M.C., Garcia Ruano J.L., Martin A., Pedregal C., Rodrigues J.H., Rubio A., Sanchez J., and Solladie G. J. Org. Chem. 55 (1990) 2120
18. Okino T., Matsuda H., Murakami M., and Yamaguchi K. Tetrahedron Lett. 34 (1993) 501
19. Ishida K., Kato T., Murakami M., Watanabe M., and Watanabe M.F. Tetrahedron 56 (2000) 8643
20. Ishida K., Matsuda H., and Murakami M. Tetrahedron 54 (1998) 13475
21. Suda H., Takita T., Aoyagi T., and Umezawa H. Antibiotics 26 (1976) 100
22. Bergmeier S.C., and Stanchina D.M. J. Org. Chem. 64 (1999) 2852
23. Sugimura H., Miura M., and Yamada N. Tetrahedron: Asymmetry 8 (1997) 4089
24. Righi G., Chionne A., D'Achille R., and Bonini C. Tetrahedron: Asymmetry 8 (1997) 903
25. Wee A.G.H., and McLeod D.D. J. Org. Chem. 68 (2003) 6268
26. Jefford C.W., Mcnulty J., Lu Z.H., and Wang J.B. Helv. Chim. Acta 79 (1996) 1203
27. Tuch A., Saniere M., Merrer Y.L., and Depezay J. Tetrahedron: Asymmetry 7 (1996) 2901
28. Ha H.J., Ahn Y.-G., Woo J.-S., Lee G.S., and Lee W.K. Bull. Chem. Soc. Jpn. 74 (2001) 1667
29. Bunnage M.E., Burke A.J., Davies S.G., and Goodwin C.J. Tetrahedron: Asymmetry 5 (1994) 203-206
30. Matsuura F., Hamada Y., and Shioiri T. Tetrahedron 50 (1994) 11303
31. Shirode N.M., Rakeeb A., and Deshmukh A.S. Tetrahedron 62 (2006) 4615
32. Wassermann H.H., Xia M., Peterson A.K., Jorgensen M.R., and Curtis E.A. Tetrahedron Lett. 40 (1999) 6163 and references cited therein
33. Raghavan S., and Joseph S.C. Tetrahedron: Asymmetry 14 (2003) 101
34. Weinreb S.M., Garigapati R.S., and Gainor J.A. Heterocycles 21 (1984) 309
35. Garigipati R.S., Freyer A.J., Whittle R.R., and Weinreb S.M. J. Am. Chem. Soc. 106 (1984) 7861
36. The reaction of 4 with CbzNSO was attempted in different solvents to determine the stereoselectivity and acetonitrile was found to be the best in terms of yield and diastereoselectivity. {A table is presented}
37. The inversion of sulfur configuration is based on our earlier work using N-Ts sulfilimine as the intramolecular nucleophile, see Ref. 6. The syn disposition of the substituents at C2 and C3 in 7a was proven by NOE studies on the acetonide derived from 15.
38. The result obtained herein is in contrast to that reported by Garcia-Ruano and co-workers (Ref. 5a) who report recovery of the starting material from a syn-amino alcohol derivative.
39. Bal B.S., Childers Jr. W.E., and Pinnick H.W. Tetrahedron 37 (1981) 2091
40. Herranz R., Castro-Pichel J., and Garcia-Lopez T. Synthesis (1989) 703