Chiral lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reactions of nitrogen-stabilized oxyallyl cations derived from allenamides

Journal of the American Chemical Society

Volumn 127, Issue 1, 2005, Pages 50-51

  Huang, Jian ^a   Hsung, Richard P ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIMETHYL FURAN; ALLYL COMPOUND; AMIDE; CATION; FURAN DERIVATIVE; LEWIS ACID; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; MOLECULAR MODEL;

EID: 11844292822     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044760b     Document Type: Article

References (53)

1. For a review, see: Hsung, R. P.; Wei, L.-L.; Xiong, H. Acc. Chem. Res. 2003, 36, 773.
2. For recent allenamide chemistry, see: (a) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (b) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (c) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964 and references therein.
3. For recent allenamide chemistry, see: (a) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (b) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (c) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964 and references therein.
4. For recent allenamide chemistry, see: (a) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (b) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (c) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964 and references therein.
5. For recent allenamide chemistry, see: (a) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (b) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (c) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964 and references therein.
6. For recent allenamide chemistry, see: (a) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (b) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (c) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964 and references therein.
7. For recent allenamide chemistry, see: (a) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229. (b) Ranslow, P. D. B.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2004, 69, 105. (c) Gaul C.; Seebach, D. Helv. Chim. Acta 2002, 85, 963. (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499. (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2001, 42, 4869. (d) Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 964 and references therein.
8. For our recent efforts, see: (a) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (b) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (c) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (d) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (e) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
9. For our recent efforts, see: (a) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (b) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (c) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (d) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (e) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
10. For our recent efforts, see: (a) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (b) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (c) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (d) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (e) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
11. For our recent efforts, see: (a) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (b) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (c) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (d) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (e) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
12. For our recent efforts, see: (a) Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629. (b) Rameshkumar, C.; Hsung, R. P. Synlett 2003, 1241. (c) Berry, C. R.; Rameshkumar, C.; Tracey, M. R.; Wei, L.-L.; Hsung, R. P. Synlett 2003, 791. (d) Rameshkumar, C.; Xiong, H.; Tracey, M. R.; Berry, C. R.; Yao, L. J.; Hsung, R. P. J. Org. Chem. 2002, 67, 1339. (e) Xiong, H.; Hsung, R. P.; Wei, L.-L.; Berry, C. R.; Mulder, J. A.; Stockwell, B. Org. Lett. 2000, 2, 2869.
13. Xiong, H.; Hsung, R. P.; Berry, C. R.; Rameshkumar, C. J. Am. Chem. Soc. 2001, 123, 7174.
14. (a) Rameshkumar, C.; Hsung, R. P. Angew. Chem., Int. Ed. 2004, 43, 615.
15. (b) Xiong, H.; Huang, J.; Ghosh, S.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694.
16. (a) Saez, J. A.; Arno, M.; Domingo, L. R. Org. Lett. 2003, 5, 4117.
17. (b) Funk, R. L.; Aungst. R. A. Org. Lett. 2001, 3, 3553.
18. (c) Harmata, M.; Sharma, U. Org. Lett. 2000, 2, 2703.
19. (d) Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 1724.
20. (e) Lee, K.; Cha, J. K. Org. Lett. 1999, 1, 523.
21. For recent reviews on [4 + 3] cycloadditions: (a) Harmata, M.; Rashatasakhon, P. Tetrahedron 2003, 59, 2371. (b) Davies, H. M. L. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: 1998; Vol. 5, pp 119-164. (c) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Grennwich, 1997; Vol. 4, pp 41-86. (d) West, F. G. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Grennwich, 1997; Vol. 4, pp 1-40.
22. For recent reviews on [4 + 3] cycloadditions: (a) Harmata, M.; Rashatasakhon, P. Tetrahedron 2003, 59, 2371. (b) Davies, H. M. L. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: 1998; Vol. 5, pp 119-164. (c) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Grennwich, 1997; Vol. 4, pp 41-86. (d) West, F. G. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Grennwich, 1997; Vol. 4, pp 1-40.
23. For recent reviews on [4 + 3] cycloadditions: (a) Harmata, M.; Rashatasakhon, P. Tetrahedron 2003, 59, 2371. (b) Davies, H. M. L. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: 1998; Vol. 5, pp 119-164. (c) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Grennwich, 1997; Vol. 4, pp 41-86. (d) West, F. G. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Grennwich, 1997; Vol. 4, pp 1-40.
24. For recent reviews on [4 + 3] cycloadditions: (a) Harmata, M.; Rashatasakhon, P. Tetrahedron 2003, 59, 2371. (b) Davies, H. M. L. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: 1998; Vol. 5, pp 119-164. (c) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Grennwich, 1997; Vol. 4, pp 41-86. (d) West, F. G. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Grennwich, 1997; Vol. 4, pp 1-40.
25. Harmata, M. Rec. Res. Dev. Org. Chem. 1997, 1, 523-535.
26. For an excellent review, see: Harmata, M. Acc. Chem. Res. 2001, 34, 595.
27. (a) Dennis, N.; Ibrahim, B.; Katritzky, A. R. J. Chem. Soc., Perkin Trans. 1 1976, 2307.
28. (b) Walters, M. A.; Arcand, H. R. J. Org. Chem. 1996, 61, 1478.
29. (c) Myers, A. G.; Barbay, J. K. Org. Lett. 2001, 3, 425.
30. For the sole account, see: Harmata, M.; Ghosh, S. K.; Hong, X.; Wacharasindu, S.; Kirchhoefer, P. J. Am. Chem. Soc. 2003, 125, 2058.
31. For recent stereoselective attempts: (a) Grainger, R. S.; Owoare, R. B.; Tisselli, P.; Steed, J. W. J. Org. Chem. 2003, 68, 7899. (b) Montanã, A. M.; Grima, P. M. Tetrahedron 2002, 58, 4769.
32. For recent stereoselective attempts: (a) Grainger, R. S.; Owoare, R. B.; Tisselli, P.; Steed, J. W. J. Org. Chem. 2003, 68, 7899. (b) Montanã, A. M.; Grima, P. M. Tetrahedron 2002, 58, 4769.
33. (a) Beck, H.; Stark, C. B. W.; Hoffman, H. M. R. Org. Lett. 2000, 2, 883 and ref 11 cited therein.
34. (b) Harmata, M.; Jones, D. E.; Kahraman, M.; Sharma, U.; Barnes, C. L. Tetrahedron Lett. 1999, 40, 1831.
35. Cho, S. Y.; Lee, J. C.; Cha, J. K. J. Org. Chem. 1999, 64, 3394.
36. (d) Davis, H. M. L.; Stafford, D. G.; Doan, B. D.; Houser, J. H. J. Am. Chem. Soc. 1998, 120, 3326.
37. For an elegant example of achiral template-based asymmetric catalysis, see: Sibi, M. P.; Zhang, R.; Manyem, S. J. Am. Chem. Soc. 2003, 125, 9306.
38. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
39. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
40. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
41. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
42. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
43. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
44. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
45. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
46. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
47. For ligand 11, see: (a) Huang, Y.; Iwama, T.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 5950. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. 12: (c) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. 13a-c, 14: (d) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325. (e) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500. (f) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horlhata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846. 15a: (g) Φstergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083. 15b: (h) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215. 16: (i) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. For a review on Lewis acids, see: (j) Yamamoto, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
48. (a) Absolute configuration of 8-5 was assigned via the single-crystal X-ray structure of a chiral ester derivative. (b) See Supporting Information for the cleavage of the oxazolidinone auxiliary and also see ref 20.
49. For a key reference, see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
50. Syn or anti isomer could be readily assigned using COSY.
51. Harmata, M.; Rashatasakhon, R. Synlett 2000, 1419.
52. Honda, T.; Ishikawa, F. Chem. Commun. 1999, 1065.
53. 2-symmetric ligands in asymmetric catalysis, see: Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.