Catalytic enantioselective alkynylation of prochiral sp3 C-H bonds adjacent to a nitrogen atom

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4997-4999

  Li, Zhiping ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; COPPER; HYDROGEN; NITROGEN; TETRAHYDROISOQUINOLINE DERIVATIVE;

ALKYNYLATION; ARTICLE; ATOM; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; HYDROGEN BOND;

ACETYLENE; ALKYNES; CATALYSIS; COPPER; ISOQUINOLINES; MOLECULAR STRUCTURE; NITROGEN; STEREOISOMERISM;

EID: 12344286967     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047814v     Document Type: Article

References (25)

1. For representative reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (b) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (d) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879. (e) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
2. For representative reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (b) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (d) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879. (e) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
3. For representative reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (b) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (d) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879. (e) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
4. For representative reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (b) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (d) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879. (e) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
5. For representative reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (b) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (d) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879. (e) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
6. For asymmteric addition of aryl C-H bond, see: Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192 and references therein. For asymmetric addition of alkynyl C-H bonds, see: Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For asymmetric aldol-type addition, see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (b) Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660. (c) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685 and references therein.
7. For asymmteric addition of aryl C-H bond, see: Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192 and references therein. For asymmetric addition of alkynyl C-H bonds, see: Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For asymmetric aldol-type addition, see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (b) Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660. (c) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685 and references therein.
8. For asymmteric addition of aryl C-H bond, see: Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192 and references therein. For asymmetric addition of alkynyl C-H bonds, see: Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For asymmetric aldol-type addition, see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (b) Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660. (c) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685 and references therein.
9. For asymmteric addition of aryl C-H bond, see: Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192 and references therein. For asymmetric addition of alkynyl C-H bonds, see: Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For asymmetric aldol-type addition, see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (b) Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660. (c) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685 and references therein.
10. For asymmteric addition of aryl C-H bond, see: Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192 and references therein. For asymmetric addition of alkynyl C-H bonds, see: Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For asymmetric aldol-type addition, see: (a) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65. (b) Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660. (c) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685 and references therein.
11. (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem., Int. Ed. 2002, 41, 2197.
12. (b) Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063.
13. (c) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509.
14. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
15. (a) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341.
16. (b) Bentley, K. W. Nat. Prod. Rep. 2004, 21, 395.
17. Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
18. (a) McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
19. (b) Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2002, 124, 5638.
20. (a) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763.
21. (b) Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem. Eur. J. 2003, 9, 2797.
22. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
23. See the Supporting Information.
24. Le, J. C.-D.; Pagenkopf, B. L. Org. Lett. 2004, 6, 4097.
25. Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409.