Asymmetric Construction of Quaternary Centers by Enantioselective Allylation: Application to the Synthesis of the Serotonin Antagonist LY426965

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1951-1953

  Denmark, Scott E ^a   Fu, Jiping ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BICYCLO(3.3.1)NONANE; BRIDGED COMPOUND; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LY 426965; PIPERIDINE DERIVATIVE; SEROTONIN ANTAGONIST;

ARTICLE; CATALYSIS; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS; BRIDGED COMPOUNDS; CATALYSIS; INDICATORS AND REAGENTS; PIPERIDINES; SEROTONIN ANTAGONISTS; STEREOISOMERISM;

EID: 0037198782     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025971t     Document Type: Article

References (19)

1. For recent review on allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (b) Chelmer, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J.; Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21; Helmchen, G., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme; Stuttgart, 1996; Vol. 3, pp 1357-1602. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
2. For recent review on allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (b) Chelmer, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J.; Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21; Helmchen, G., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme; Stuttgart, 1996; Vol. 3, pp 1357-1602. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
3. For recent review on allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (b) Chelmer, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J.; Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21; Helmchen, G., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme; Stuttgart, 1996; Vol. 3, pp 1357-1602. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
4. For recent review on allylmetal additions, see: (a) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 10. (b) Chelmer, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J.; Ed.; Wiley-VCH: Weinheim, 2000; Chapter 11. (c) Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Edition E21; Helmchen, G., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme; Stuttgart, 1996; Vol. 3, pp 1357-1602. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
5. For the most recent advance in chiral Lewis-base-catalyzed enantioselective allylation, see: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 and reference therein. While this manuscript was in preparation, Hall reported the generation of quaternary centers using chiral allylboronate reagents. (b) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898.
6. For the most recent advance in chiral Lewis-base-catalyzed enantioselective allylation, see: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 and reference therein. While this manuscript was in preparation, Hall reported the generation of quaternary centers using chiral allylboronate reagents. (b) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898.
7. For reviews on enantioselective construction of quaternary stereocenters, see: (a) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (c) Fuji, K. Chem. Rev. 1993, 93, 2037. (d) Martin, S. F. Tetrahedron 1980, 36, 419.
8. For reviews on enantioselective construction of quaternary stereocenters, see: (a) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (c) Fuji, K. Chem. Rev. 1993, 93, 2037. (d) Martin, S. F. Tetrahedron 1980, 36, 419.
9. For reviews on enantioselective construction of quaternary stereocenters, see: (a) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (c) Fuji, K. Chem. Rev. 1993, 93, 2037. (d) Martin, S. F. Tetrahedron 1980, 36, 419.
10. For reviews on enantioselective construction of quaternary stereocenters, see: (a) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (c) Fuji, K. Chem. Rev. 1993, 93, 2037. (d) Martin, S. F. Tetrahedron 1980, 36, 419.
11. (a) Rasmussen, K.; Calligaro, D. O.; Czachura, J. F.; Dreshfield-Ahmad, L. J.; Evans, D. C.; Hemrick-Luecke, S. K.; Kallman, M. J.; Kendrick, W. T.; Leander, J. D.; Nelson, D. L.; Overshiner, C. D.; Wainscott, D. B.; Wolff, M. C.; Wong, D. T.; Branchek, T. A.; Zgombick, J. M.; Xu, Y.-C. J. Pharmacol. Exp. Ther. 2000, 294, 688.
12. (b) Kohlman, T. D.; Xu, Y.-C.; Godfrey, A. G.; O'Toole, J. C.; Zhang, T. Y. Eur. Pat. Appl. 1999, 47pp.
13. For recent examples, see: (a) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261. (b) Saito, S.; Nakadai, M.; Yamamoto, H. Synlett 2000, 1107.
14. For recent examples, see: (a) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261. (b) Saito, S.; Nakadai, M.; Yamamoto, H. Synlett 2000, 1107.
15. Okudado, N.; Negishi, E.-I. Tetrahedron Lett. 1978, 27, 2357.
16. Short, J. D.; Attenoux, S.; Berrisford, D. J. Tetrahedron Lett. 1997, 38, 2351.
17. Formation of chlorohydrins has also been observed in other reactions of chlorosilanes with aldehydes: Wynn, T.; Ghosh, S. K. Unpublished results from these laboratories.
18. For mechanistic studies, see: (a) Denmark, S. E.; Su, X.; Nishigaichi, Y. J. Am. Chem. Soc. 1998, 120, 12990. (b) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021.
19. For mechanistic studies, see: (a) Denmark, S. E.; Su, X.; Nishigaichi, Y. J. Am. Chem. Soc. 1998, 120, 12990. (b) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021.