Asymmetric synthesis of acyclic amines through Zr- and Hf-catalyzed enantioselective alkylzinc reagents to imines

Advanced Synthesis and Catalysis

Volumn 347, Issue 2-3, 2005, Pages 417-425

  Akullian, Laura C ^a   Porter, James R ^a   Traverse, John F ^a   Snapper, Marc L ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

Asymmetric alkylation; Asymmetric catalysis; Chiral amines; Hafnium; Imines; Zirconium

Indexed keywords

ALIPHATIC COMPOUND; AMINE; AMINO ACID; AROMATIC COMPOUND; HAFNIUM; IMINE; INORGANIC SALT; LEWIS ACID; LIGAND; METAL; NITROGEN; REAGENT; ZINC DERIVATIVE; ZIRCONIUM;

ACIDITY; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MECHANICS; MODEL; OPTICS; PURIFICATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 15044340854     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404319     Document Type: Article

References (54)

1. For representative examples, see: a) S. J. Degrade, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 755-756; b) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781; c) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; d) A. W. Hird, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 1276-1279; e) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691; e) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681; f) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832; for a brief overview, see: g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
2. For representative examples, see: a) S. J. Degrade, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 755-756; b) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781; c) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; d) A. W. Hird, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 1276-1279; e) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691; e) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681; f) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832; for a brief overview, see: g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
3. For representative examples, see: a) S. J. Degrade, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 755-756; b) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781; c) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; d) A. W. Hird, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 1276-1279; e) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691; e) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681; f) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832; for a brief overview, see: g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
4. For representative examples, see: a) S. J. Degrade, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 755-756; b) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781; c) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; d) A. W. Hird, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 1276-1279; e) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691; e) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681; f) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832; for a brief overview, see: g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
5. For representative examples, see: a) S. J. Degrade, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 755-756; b) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781; c) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; d) A. W. Hird, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 1276-1279; e) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691; e) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681; f) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832; for a brief overview, see: g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
6. For representative examples, see: a) S. J. Degrade, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 755-756; b) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781; c) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; d) A. W. Hird, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 1276-1279; e) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691; e) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681; f) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832; for a brief overview, see: g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
7. For representative examples, see: a) S. J. Degrade, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 755-756; b) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781; c) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; d) A. W. Hird, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 1276-1279; e) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691; e) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681; f) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832; for a brief overview, see: g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
8. For representative examples, see: a) S. J. Degrade, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 755-756; b) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781; c) C. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; d) A. W. Hird, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 1276-1279; e) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691; e) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681; f) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832; for a brief overview, see: g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
9. H. Deng, M. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. Int. Ed. 2002, 41, 1009-1012.
10. For representative examples, see: a) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285; b) J. R. Porter, K. W. Kuntz, W. Wirschun, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 2657-2658; c) N. S. Josephsohn, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 11594-11599; d) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018-4019; e) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734-3735.
11. For representative examples, see: a) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285; b) J. R. Porter, K. W. Kuntz, W. Wirschun, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 2657-2658; c) N. S. Josephsohn, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 11594-11599; d) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018-4019; e) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734-3735.
12. For representative examples, see: a) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285; b) J. R. Porter, K. W. Kuntz, W. Wirschun, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 2657-2658; c) N. S. Josephsohn, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 11594-11599; d) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018-4019; e) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734-3735.
13. For representative examples, see: a) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285; b) J. R. Porter, K. W. Kuntz, W. Wirschun, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 2657-2658; c) N. S. Josephsohn, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 11594-11599; d) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018-4019; e) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734-3735.
14. For representative examples, see: a) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285; b) J. R. Porter, K. W. Kuntz, W. Wirschun, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 2657-2658; c) N. S. Josephsohn, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 11594-11599; d) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018-4019; e) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734-3735.
15. For a review of Zr-catalyzed enantioselective reactions, see: A. H. Hoveyda, in: Titanium and Zirconium in Organic Synthesis, (Ed.: I. Marek), VCH-Wiley, Weinheim, 2002, pp. 180-229.
16. a) J. R. Porter, J. F. Traverse, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 984-985;
17. b) J. R. Porter, J. F. Traverse, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 10409-10410;
18. c) J. F. Traverse, A. H. Hoveyda, M. L. Snapper, Org. Lett. 2003, 5, 3273-3275;
19. d) L. C. Akullian, M. L. Snapper, A. H. Hoveyda, Angew. Chem. Int. Ed. 2003, 42, 4244-4247.
20. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
21. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
22. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
23. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
24. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
25. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
26. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
27. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
28. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
29. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
30. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
31. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
32. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
33. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
34. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
35. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
36. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
37. For studies carried out in other laboratories in connection with catalytic asymmetric alkylations of imines, see: a) S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878 and references cited therein; b) H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc. 2000, 122, 12055-12056; c) I. Sato, R. Kodaka, K. Soai, J. Chem. Soc. Perkin Trans. 1, 2001, 2912-2914; d) S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941; e) N. Hermanns, S. Dahmen, C. Bolm, S. Bräse, Angew. Chem. Int. Ed. 2002, 41, 3692-3694, f) H-L. Zhang, X-M. Zhang, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, M. C. K. Choi, A. S. C. Chan, Org. Lett. 2002, 4, 1399-1400; g) K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, K. Tomioka, Chem. Lett. 2002, 8-9; h) A. A. Boezio, A. B. Charrette, J. Am. Chem. Soc. 2003, 125, 1692-1693; i) X-M. Zhang, H-L. Zhang, W-Q. Lin, L-Z. Gong, A-Q. Mi, X. Cui, Y-Z. Jiang, K-B. Yu, J. Org. Chem. 2003, 68, 4322-4330; j) X. Li, L-F. Cun, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821; k) T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727; l) A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, J. Am. Chem. Soc. 2003, 125, 14260-14261; m) M. Shi, W. Zhang, Tetrahedron: Asymmetry 2003, 14, 3407-3414; n) M. Shi, C-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973; o) C-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237; p) N. Cabello, J-C. Kizirian, A. Alexakis, Tetrahedron Lett. 2004, 45, 4639-4642; q) H-L. Zhang, F. Jiang, X-M. Zhang, X. Cui, L-Z. Gong, A-Q. Mi, Y-Z. Jiang, Y-D. Wu, Chem. Eur. J. 2004, 10, 1481-1492; r) S. J. Patel, T. F. Jamieson, Angew. Chem. Int. Ed. 2004, 43, 3941-3944.
38. For reviews of catalytic asymmetric additions to imines, see: a) D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946; b) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094.
39. For reviews of catalytic asymmetric additions to imines, see: a) D. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946; b) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094.
40. Boc-L-Val and Boc-L-Phe are commercially available at $ 0.15 and $ 0.19 per mmol from Advanced Chem tech; the corresponding D-isomers can be purchased at $ 1.22 and $ 0.86 per mmol.
41. [5b]
42. See the Supporting Information for experimental details and spectroscopic data.
43. [5d] depending on the class of imine stubstrates, a different type of o-aniline activating group may well prove to be the optimal choice (e.g., o-phenoxyanilines for additions to alkynylimines). The present discussion pertains largely to aryl- and alkylimine substrates.
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