δ-Amino β-keto Esters, a designed polyfunctionalized chiral building block for alkaloid synthesis. Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1041-1043

  Davis, Franklin A ^a   Chao, Bin ^a   Fang, Tianan ^a   Szewczyk, Joanna M ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLPIPERIDINE; 2-PHENYLPIPERIDINE; ALKALOID; ESTER; PIPERIDINE DERIVATIVE; SS 20846A;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKALOIDS; ESTERS; PIPERIDINES;

EID: 0034689892     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005580j     Document Type: Article

References (38)

1. (a) Hanessian, S. Total Synthesis of Natural Products: the 'Chiron' Approach; Pergamon: Oxford 1983.
2. (b) Banfi, L.; Guanti, G. Synthesis 1993, 1029
3. (a) Johnson, C. R. Acc. Chem. Res. 1998, 31, 333.
4. (b) Murphy, S. T.; Bencsik, J. R.; Johnson, C. R. Org. Lett. 1999, 1, 1483.
5. Ojima, I. Acc. Chem. Res. 1995, 28, 383.
6. Meyers, A. I.; Brengel, G. P. J. Chem. Soc., Chem. Commun. 1997, 1.
7. For reviews on sulfinimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAL Press Inc.: 2000; Vol. 2, pp 249-282.
8. (b) Hua, D. H.; Chen, Y.; Millward, G. S. Sulfur Rep. 1999, 21, 211.
9. (c) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
10. For reviews on the synthesis of substitute piperidines, see: (a) Bailey, P. D.; Millwood, P. A. Smith, P. D. J. Chem. Soc., Chem. Commun. 1998, 633.
11. (b) Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Procd. Int. 1996, 28, 499.
12. (c) Wang, C.-L. J.; Wuonola, M. A. Org. Prep. Procd. Int. 1992, 28, 585.
13. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAL Press Inc.: 1996; Vol. 2, pp 251-294.
14. Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383.
15. For references to δ-amino β-keto esters, see: (a) Li, B.; Franck, R. W. Bioorg. Med. Chem. Lett. 1999, 9, 2629.
16. (b) Werner, R. M.; Shokek, O. Davis, J. T. J. Org. Chem. 1997, 62, 8243.
17. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60, 7037.
18. For a racemic synthesis of 4, see: Ashton, M. J.; Hills, S. J.; Newton, C. G.; Taylor, J. B.; Tondu, S. C. D. Heterocycles 1989, 28, 1015.
19. For earlier asymmetric syntheses of 7, see: (a) Davis, F. A.; Szewczyk, J. M. Tetrahedron Lett. 1998, 39, 5951.
20. (b) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.
21. (c) Deziel, R.; Malenfant, E. J. J. Org. Chem. 1995, 60, 4660.
22. See, for example: (a) Rubiralta, M.; Giralt, E.; Diez, A. Piperidine Structure, Preparation, Reactivity and Synthetic Applications of Piperidine and its Derivatives; Elsevier: Amsterdam, 1991.
23. (b) Rubiralta, M.; Diez, A.; Vila, C.; Troin, Y.; Feliz, M. J. Org. Chem. 1991, 56, 6292.
24. (c) Comins, D. L.; LaMunyon, D. H. J. Org. Chem. 1992, 57, 5807.
25. (d) Diez, A.; Mavel, S.; Teulade, J. C.; Chavignon, O.; Sinibaldi, M. E.; Troin, Y.; Rubiralta, M. Heterocycles 1993, 36, 2451.
26. For leading references, see: Kudzma, L. V.; Severnak, S. A.; Benvenga, M. J.; Ezell, E. F.; Ossipov, M. H.; Knight, V. V.; Rudo, F. G.; Spencer, H. K.; Spaulding, T. C. J. Med. Chem. 1989, 32, 2534.
27. Komoto, T.; Yano, K.; Ono, J.; Okawa, J.; Nakajima, T. Jpn. Kokai 35788(20/02/1986); Chem. Abstr. 1986, 105, 132137w.
28. (a) Mayer, M.; Thiericke, R. J. Org. Chem. 1993, 58, 3486.
29. (b) Grabley, S.; Hammann, P.; Kluge, H.; Wink, J.; Kricke, P.; Zeeck, A. J. Antibiot. 1991, 44, 797.
30. Davis, F. A.; Zhang, Y. Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1043.
31. For leading references to sulfinimines (N-sulfinyl imines) chemistry, see: Davis, F. A.; Andemichael, Y. W. J. Org. Chem. 1999, 64, 8627.
32. 1H NMR.
33. Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803.
34. For earlier syntheses of 14, see: (a) Ripoche, I.; Canet, J.-L.; Aboab, B.; Gelas, J.; Troin, Y. J. Chem. Soc., Perkin Trans. 1 1998, 3485.
35. (b) Yokoyama, H.; Otaya, K.; Yamaguchi, S.; Hirai, Y. Tetrahedron Lett. 1998, 39, 5971.
36. (c) Takemoto, Y.; Ueda, S.; Takeuchi, J.; Baba, Y.; Iwata, C. Chem. Pharm. Bull. 1997, 45, 1906.
37. (d) Takemoto, Y.; Ueda, S.; Takeuchi, J.; Nakamoto, T.; Iwata, C. Tetrahedron Lett. 1994, 35, 8821.
38. 3).