Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition

Angewandte Chemie - International Edition

Volumn 44, Issue 1, 2004, Pages 105-108

  Li, Hongming ^a   Wang, Yi ^a   Tang, Liang ^a   Wu, Fanghui ^a   Liu, Xiaofeng ^a   Guo, Chengyun ^a   Foxman, Bruce M ^a   Deng, Li ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Cinchona alkaloids; Hydrogen bonding; Michael addition; Nitroalkenes

Indexed keywords

ACETOACETIC ACID; ALKENE DERIVATIVE; CARBON; CINCHONA ALKALOID; MALONIC ACID;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL MODEL; CHIRALITY; ENANTIOSELECTIVITY; HYDROGEN BOND; MICHAEL ADDITION; PROTEIN QUATERNARY STRUCTURE; RACEMIC MIXTURE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 11244281650     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461923     Document Type: Article

References (22)

1. For reviews see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171; c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726; Angew. Chem. Int. Ed. 2003, 42, 1688; e) J. Christoffers, Chem. Eur. J. 2003, 9, 4862; f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363; g) M. Yamaguchi in Comprehensive Asymmetric Catalysisis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2003, Suppl. 1, Supplement to chap. 31.2, p. 151.
2. For reviews see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171; c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726; Angew. Chem. Int. Ed. 2003, 42, 1688; e) J. Christoffers, Chem. Eur. J. 2003, 9, 4862; f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363; g) M. Yamaguchi in Comprehensive Asymmetric Catalysisis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2003, Suppl. 1, Supplement to chap. 31.2, p. 151.
3. For reviews see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171; c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726; Angew. Chem. Int. Ed. 2003, 42, 1688; e) J. Christoffers, Chem. Eur. J. 2003, 9, 4862; f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363; g) M. Yamaguchi in Comprehensive Asymmetric Catalysisis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2003, Suppl. 1, Supplement to chap. 31.2, p. 151.
4. For reviews see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171; c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726; Angew. Chem. Int. Ed. 2003, 42, 1688; e) J. Christoffers, Chem. Eur. J. 2003, 9, 4862; f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363; g) M. Yamaguchi in Comprehensive Asymmetric Catalysisis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2003, Suppl. 1, Supplement to chap. 31.2, p. 151.
5. For reviews see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171; c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726; Angew. Chem. Int. Ed. 2003, 42, 1688; e) J. Christoffers, Chem. Eur. J. 2003, 9, 4862; f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363; g) M. Yamaguchi in Comprehensive Asymmetric Catalysisis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2003, Suppl. 1, Supplement to chap. 31.2, p. 151.
6. For reviews see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171; c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726; Angew. Chem. Int. Ed. 2003, 42, 1688; e) J. Christoffers, Chem. Eur. J. 2003, 9, 4862; f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363; g) M. Yamaguchi in Comprehensive Asymmetric Catalysisis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2003, Suppl. 1, Supplement to chap. 31.2, p. 151.
7. For reviews see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171; c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726; Angew. Chem. Int. Ed. 2003, 42, 1688; e) J. Christoffers, Chem. Eur. J. 2003, 9, 4862; f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363; g) M. Yamaguchi in Comprehensive Asymmetric Catalysisis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2003, Suppl. 1, Supplement to chap. 31.2, p. 151.
8. For reviews see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171; c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726; Angew. Chem. Int. Ed. 2003, 42, 1688; e) J. Christoffers, Chem. Eur. J. 2003, 9, 4862; f) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363; g) M. Yamaguchi in Comprehensive Asymmetric Catalysisis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2003, Suppl. 1, Supplement to chap. 31.2, p. 151.
9. a) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11 204;
10. b) J. F. Austin, S.-G. Kim, C. J. Sinz, W.-J. Xiao, D. W. C. MacMillan, Proc. Natl. Acad. Sci USA, 2004, 101, 5482.
11. For other notable studies of intermolecular, diastereoselective, and enantioselective catalytic conjugate additions for the construction of vicinal quaternary and tertiary stereocenters see: a) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11 240; b) M. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 2527.
12. For other notable studies of intermolecular, diastereoselective, and enantioselective catalytic conjugate additions for the construction of vicinal quaternary and tertiary stereocenters see: a) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11 240; b) M. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 2527.
13. H. Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906.
14. For other recent examples of highly enantioselective Michael additions catalyzed by cinchona alkaloid derivatives see: a) P. McDaid, Y. Chen, L. Deng, Angew. Chem. 2002, 114, 348; Angew. Chem. Int. Ed. 2002, 41, 348; b) M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 5672.
15. For other recent examples of highly enantioselective Michael additions catalyzed by cinchona alkaloid derivatives see: a) P. McDaid, Y. Chen, L. Deng, Angew. Chem. 2002, 114, 348; Angew. Chem. Int. Ed. 2002, 41, 348; b) M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 5672.
16. For other recent examples of highly enantioselective Michael additions catalyzed by cinchona alkaloid derivatives see: a) P. McDaid, Y. Chen, L. Deng, Angew. Chem. 2002, 114, 348; Angew. Chem. Int. Ed. 2002, 41, 348; b) M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 5672.
17. See the Supporting Information for details.
18. Catalyst 6 was first reported by Hatakeyama et al. See: a) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10 219; b) S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, S. Hatakeyama, Org. Lett. 2003, 5, 3103.
19. Catalyst 6 was first reported by Hatakeyama et al. See: a) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10 219; b) S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, S. Hatakeyama, Org. Lett. 2003, 5, 3103.
20. For the use of conformationally rigid cinchona alkaloids to probe the active conformer of cinchona alkaloids as ligands for Os-catalyzed Sharpless asymmetric dihydroxylations see: a) E. J. Corey, M. C. Noe, J. Am. Chem. Soc. 1993, 115, 12 579; b) E. J. Corey, M. C. Noe, J. Am. Chem. Soc. 1996, 118, 11 038.
21. For the use of conformationally rigid cinchona alkaloids to probe the active conformer of cinchona alkaloids as ligands for Os-catalyzed Sharpless asymmetric dihydroxylations see: a) E. J. Corey, M. C. Noe, J. Am. Chem. Soc. 1993, 115, 12 579; b) E. J. Corey, M. C. Noe, J. Am. Chem. Soc. 1996, 118, 11 038.
22. For a study of the active conformer of cinchona alkaloids in applications as an organic catalyst see: G. S. Cortez, S. H. Oh, D. Romo, Synthesis 2001, 1731.