Diastereoselective Addition Reactions of Furyl Sulfonylimine Using Chiral Boronates as Auxiliary: Application to the Enantioselective Synthesis of 2,3-Disubstituted Furyl Sulfonylamides

Journal of Organic Chemistry

Volumn 69, Issue 8, 2004, Pages 2892-2895

  Yim, Ho Kee ^a   Wong, Henry N C ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINES; BORON COMPOUNDS; CHEMICAL BONDS; CHROMATOGRAPHIC ANALYSIS;

DIASTEREOMERS; DIASTEREOSELECTIVITY;

STEREOCHEMISTRY;

BORON DERIVATIVE; IMINE; SULFANILAMIDE DERIVATIVE; SULFONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CHIRALITY; CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOSELECTIVITY; OPTICAL ROTATION; REACTION ANALYSIS; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 1842638263     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030385e     Document Type: Article

References (30)

1. (a) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
2. (b) Yang, C. F.; Liao, L. X.; Xu, Y. M.; Zhang, H. X.; Xia, P.; Zhou, W. S. Tetrahedron: Asymmetry 1999, 10, 2311.
3. (c) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619.
4. (d) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135.
5. (a) Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2001, 3, 401.
6. (b) Koriyama, Y.; Nozawa, A.; Hayakawa, R.; Shimizu, M. Tetrahedron 2002, 58, 9621.
7. (c) Zhang, H. X.; Xia, P.; Zhou, W. S. Tetrahedron 2003, 59, 2015.
8. (a) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105.
9. (b) Achmatowicz, O., Jr.; Bukowski, P.; Szechner, B.; Zwierzchowska, Z.; Zamojski, A. Tetrahedron 1971, 27, 1973.
10. (a) Bushey, M. L.; Haukaas, M. H.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2984.
11. (b) Zhou, W. S.; Lu, Z. H.; Wang, Z. M. Tetrahedron 1993, 49, 2641.
12. (c) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
13. (d) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.
14. (e) Koriyama, Y.; Nozawa, A.; Hayakawa, R.; Shimizu, M. Tetrahedron 2002, 58, 9621.
15. Nakayama, K.; Rainer, J. D. Tetrahedron 1990, 46, 4165.
16. (a) Luithle, J. E. A.; Pietruszka, J. J. Org. Chem. 2000, 65, 9194.
17. (b) Luithle, J. E. A.; Pietruszka, J. Eur. J. Org. Chem. 2000, 2557.
18. (c) Luithle, J. E. A.; Pietruszka, J. J. Org. Chem. 1999, 64, 8287.
19. (d) Luithle, J. E. A.; Pietruszka, J.; Witt, A. J. Chem. Soc., Chem. Commun. 1998, 2651.
20. (a) Chan, K. F.; Wong, H. N. C. Org. Lett. 2001, 3, 3991.
21. (b) Chan, K. F.; Wong, H. N. C. Eur. J. Org. Chem. 2003, 82.
22. Wong, M. K.; Leung, C. Y.; Wong, H. N. C. Tetrahedron 1997, 53, 3497.
23. Courtesy of Prof. Yundong Wu, The Hong Kong University of Science and Technology.
24. See the Supporting Information.
25. (a) Yamaguchi, M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, p 325.
26. (b) Volmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; p 355.
27. (c) Stork, G.; Dowd, S. R. J. Am. Chem. Soc. 1963, 85, 2178.
28. Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: London, 1995; Chapter 1.
29. (a) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 893.
30. (b) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; VCH: Weinheim, 1997.