N-sulfinyl β-amino Weinreb amides: Synthesis of enantiopure β-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine

Organic Letters

Volumn 5, Issue 6, 2003, Pages 925-927

  Davis, Franklin A ^a   Prasad, Kavirayani R ^a   Nolt, M Brad ^a   Wu, Yongzhong ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; AMIDE; CARBONYL DERIVATIVE; IMINE; N METHYLACETAMIDE; POTASSIUM; SEDRIDINE; UNCLASSIFIED DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PIPERIDINE DERIVATIVE; SULFOXIDE;

ARTICLE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; POLYMERIZATION; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

AMIDES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; PIPERIDINES; STEREOISOMERISM; SULFOXIDES;

EID: 0038204475     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034119z     Document Type: Article

References (36)

1. For reviews, see: (a) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399. (b) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
2. For reviews, see: (a) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399. (b) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
3. For a review, see: Bates, R. W.; Sa-Ei, K. Tetrahedron 2002, 58, 5957.
4. Davis, F. A.; Szewczyk J. M., Tetrahedron Lett. 1998, 39, 5951.
5. Louis, C.; Mill, S,; Mancuso, V.; Hootele, C. Can. J. Chem. 1994, 72, 1347.
6. Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229.
7. (a) Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Len. 1990, 31, 5153.
8. (b) Rodriguez, M.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 7319.
9. (c) Limal, D.; Quesnel, A.; Briand, J.-P. Tetrahedron Lett. 1998, 39, 4239.
10. Toujas, J.-L.; Toupet, L.; Vaultier, M. Tetrahedron 2000, 56, 2665.
11. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 2911.
12. Asymmetric synthesis of β-amino carbonyl compounds: reduction of β-amino esters or nitriles, see refs 3 and 8 of this article. Toujas, J.-L.; Jost, E., Vaultier, M. Bull. Soc. Chem. Fr, 1997, 134, 713. Arndt-Eistert reaction, see ref 6 of this article.
13. (a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
14. (b) For an excellent review on applications of Weinreb amides, see: Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15.
15. (a) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodrigues-Solla, H. Synlett 2002, 1146.
16. (b) Davies, S. G.; McCarthy, T. D. Synlett. 1995, 700.
17. (c) Ref 6 of this article.
18. Results of these studies will be reported separately in due course.
19. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60, 7037.
20. For reviews on the chemistry of sulfinimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen. B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
21. For reviews on the chemistry of sulfinimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen. B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
22. For reviews on the chemistry of sulfinimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen. B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
23. For reviews on sedum and related alkaloids, see: (a) ref 2. (b) Strunz, G. M.; Findlay, J. A. Pyridine and Piperidine Alkaloids. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-174.
24. For reviews on sedum and related alkaloids, see: (a) ref 2. (b) Strunz, G. M.; Findlay, J. A. Pyridine and Piperidine Alkaloids. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-174.
25. Meth-Cohn, O.; Yu, C.-Y.: Lestage, P.; M.-C.; Cagniard, D.-H.; Renard, P. Eur. Pat. 1050531, 2000.
26. For asymmetric syntheses of these alkaloids, see: (a) Takahata, H.; Kubota, M.; Ikota, N. J. Org. Chem. 1999, 64, 8594. (b) Louis, C.; Hottele, C. Tetrahedron: Asymmetry 1997, 8, 109. (c) Littler, B. J.; Gallagher, T.; Boddy, I. K.; Riordan, P. D. Synlett 1997, 22.
27. For asymmetric syntheses of these alkaloids, see: (a) Takahata, H.; Kubota, M.; Ikota, N. J. Org. Chem. 1999, 64, 8594. (b) Louis, C.; Hottele, C. Tetrahedron: Asymmetry 1997, 8, 109. (c) Littler, B. J.; Gallagher, T.; Boddy, I. K.; Riordan, P. D. Synlett 1997, 22.
28. For asymmetric syntheses of these alkaloids, see: (a) Takahata, H.; Kubota, M.; Ikota, N. J. Org. Chem. 1999, 64, 8594. (b) Louis, C.; Hottele, C. Tetrahedron: Asymmetry 1997, 8, 109. (c) Littler, B. J.; Gallagher, T.; Boddy, I. K.; Riordan, P. D. Synlett 1997, 22.
29. (a) Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1043.
30. (b) Fanelli, D. L.; Szewczyk, J. M.; Zhang, Y.; Reddy, G. V.; Burns, D. M.; Davis, F. A. Org. Synth. 1999, 77, 50.
31. For a review on the reduction of amino ketones that includes a section on the reduction of acyclic β-amino ketones, see: Tramontini, M. Synthesis 1982, 605.
32. (a) Veenstra, S. J.; Kinderman, S. S. Synlett 2001, 1109.
33. (b) Wanner, K. Th.; Hofner, G. Tetrahedron 1991, 47, 1895.
34. (c) Pilli, R. A.; Russowsky, D.; Dias, L. C. J. Chem. Soc., Perkin Trans. 1 1990, 1213.
35. (d) Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. L. J. Org. Chem. 1992, 57, 1219.
36. Greeves, N. In Comprehensive Organic Synthesis; Trost B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 8, Chapter 1, p 1.