Direct Asymmetric Synthesis of β-Amino Ketones from Sulfinimines (N-Sulfinylimines). Synthesis of (-)-Indolizidine 209B

Organic Letters

Volumn 5, Issue 26, 2003, Pages 5011-5014

  Davis, Franklin A ^a   Yang, Bin ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; IMINE; INDOLIZIDINE ALKALOID; KETONE DERIVATIVE; PIPERIDINE DERIVATIVE; POTASSIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

ALKALOIDS; IMINES; INDOLIZINES; KETONES; PIPERIDINES; STEREOISOMERISM;

EID: 0346025405     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035981+     Document Type: Article

References (36)

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13. (10) 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.
14. 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.
15. 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.
16. For a review on sulfinimine derived polyfunctionalized chiral building blocks, see: Davis, F. A.; Chao, B.; Andemichael, Y. W.; Mohanty, P. K.; Fang, T.; Burns, D. M.; Rao, A.; Szewczyk, J. M. Heteroto. Chem. 2002, 13, 48.
17. (12) For applications of N-sulfinyl δ-amino β-ketoesters to the asymmetric synthesis of piperidine and pyrrolidine alkaloids, see: (a) Davis, F. A.; Chao, Fang, T.; Szewczyk, J. M. Org. Lett. 1999, 1, 1041. (b) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599. (f) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147. (g) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
18. For applications of N-sulfinyl δ-amino β-ketoesters to the asymmetric synthesis of piperidine and pyrrolidine alkaloids, see: (a) Davis, F. A.; Chao, Fang, T.; Szewczyk, J. M. Org. Lett. 1999, 1, 1041. (b) Davis, F. A. ; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599. (f) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147. (g) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
19. For applications of N-sulfinyl δ-amino β-ketoesters to the asymmetric synthesis of piperidine and pyrrolidine alkaloids, see: (a) Davis, F. A.; Chao, Fang, T.; Szewczyk, J. M. Org. Lett. 1999, 1, 1041. (b) Davis, F. A. ; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599. (f) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147. (g) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
20. For applications of N-sulfinyl δ-amino β-ketoesters to the asymmetric synthesis of piperidine and pyrrolidine alkaloids, see: (a) Davis, F. A.; Chao, Fang, T.; Szewczyk, J. M. Org. Lett. 1999, 1, 1041. (b) Davis, F. A. ; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599. (f) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147. (g) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
21. For applications of N-sulfinyl δ-amino β-ketoesters to the asymmetric synthesis of piperidine and pyrrolidine alkaloids, see: (a) Davis, F. A.; Chao, Fang, T.; Szewczyk, J. M. Org. Lett. 1999, 1, 1041. (b) Davis, F. A. ; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599. (f) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147. (g) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
22. For applications of N-sulfinyl δ-amino β-ketoesters to the asymmetric synthesis of piperidine and pyrrolidine alkaloids, see: (a) Davis, F. A.; Chao, Fang, T.; Szewczyk, J. M. Org. Lett. 1999, 1, 1041. (b) Davis, F. A. ; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599. (f) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147. (g) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
23. For applications of N-sulfinyl δ-amino β-ketoesters to the asymmetric synthesis of piperidine and pyrrolidine alkaloids, see: (a) Davis, F. A.; Chao, Fang, T.; Szewczyk, J. M. Org. Lett. 1999, 1, 1041. (b) Davis, F. A. ; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599. (f) Davis, F. A.; Yang, B.; Deng, J. J. Org. Chem. 2003, 68, 5147. (g) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
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31. (14) For earlier syntheses of (-)-indolizidine 209B and leading references, see: (a) Ma, D.; Pu, X.; Wang, J. Tetrahedron: Asymmetry 2002, 13, 2257. (b) Song, Y.; Okamoto, S.; Sato, F. Tetrahedron Lett. 2002, 43, 8635. (c) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. (d) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543. (e) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919.
32. For earlier syntheses of (-)-indolizidine 209B and leading references, see: (a) Ma, D.; Pu, X.; Wang, J. Tetrahedron: Asymmetry 2002, 13, 2257. (b) Song, Y.; Okamoto, S.; Sato, F. Tetrahedron Lett. 2002, 43, 8635. (c) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. (d) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543. (e) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919.
33. For earlier syntheses of (-)-indolizidine 209B and leading references, see: (a) Ma, D.; Pu, X.; Wang, J. Tetrahedron: Asymmetry 2002, 13, 2257. (b) Song, Y.; Okamoto, S.; Sato, F. Tetrahedron Lett. 2002, 43, 8635. (c) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. (d) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543. (e) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919.
34. For earlier syntheses of (-)-indolizidine 209B and leading references, see: (a) Ma, D.; Pu, X.; Wang, J. Tetrahedron: Asymmetry 2002, 13, 2257. (b) Song, Y.; Okamoto, S.; Sato, F. Tetrahedron Lett. 2002, 43, 8635. (c) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. (d) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543. (e) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919.
35. For earlier syntheses of (-)-indolizidine 209B and leading references, see: (a) Ma, D.; Pu, X.; Wang, J. Tetrahedron: Asymmetry 2002, 13, 2257. (b) Song, Y.; Okamoto, S.; Sato, F. Tetrahedron Lett. 2002, 43, 8635. (c) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. (d) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543. (e) Michael, J. P.; Gravestock, D. J. Chem. Soc., Perkin Trans. 1 2000, 1919.
36. For a review, see Daly, J. W.; Carraffo, H. M.; Spande, T. F. In Alkaloids: Chemical & Biological Perspectives; Pelletier, S. W., Ed.; Pergamon Press: Oxford, 1999; Vol. 13, pp 1-161.