C2-symmetric copper(II) complexes as chiral lewis acids. Catalytic enantioselective carbonyl - Ene reactions with glyoxylate and pyruvate esters

Journal of the American Chemical Society

Volumn 122, Issue 33, 2000, Pages 7936-7943

  Evans, David A ^a   Tregay, Steven W ^a   Burgey, Christopher S ^a   Paras, Nick A ^a   Vojkovsky, Tomas ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBONYL DERIVATIVE; COPPER COMPLEX; ESTER DERIVATIVE; GLYOXYLIC ACID; INORGANIC ACID; PYRUVIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DEPOLYMERIZATION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034706033     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000913t     Document Type: Article

References (67)

1. For a general review of enantioselective ene reactions see: (a) Mikami, K.; Shimizu, M. Chem. Rev, 1992, 92, 1021-1050. (b) Dias, L. C. Curr. Org. Chem. 2000, 4, 305-342.
2. For a general review of enantioselective ene reactions see: (a) Mikami, K.; Shimizu, M. Chem. Rev, 1992, 92, 1021-1050. (b) Dias, L. C. Curr. Org. Chem. 2000, 4, 305-342.
3. Whitesell, J. K.; Bhattacharya, A.; Buchanan, C. M.; Chen, H. H.; Deyo, D.; James, D.; Liu, C-L.; Minto, M. A. Tetrahedron 1986, 42, 2993-3001 and references therein. Reaction between N-glyoxyloyl-(2R)-borane- 10,2-sultam and monosubstituted olefins has also been reported: Jezewski, A.; Chajewska, K.; Wielogórski, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 1741-1749.
4. Whitesell, J. K.; Bhattacharya, A.; Buchanan, C. M.; Chen, H. H.; Deyo, D.; James, D.; Liu, C-L.; Minto, M. A. Tetrahedron 1986, 42, 2993- 3001 and references therein. Reaction between N-glyoxyloyl-(2R)-borane-10,2-sultam and monosubstituted olefins has also been reported: Jezewski, A.; Chajewska, K.; Wielogórski, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 1741-1749.
5. Mauruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967-3970.
6. (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644.
7. (b) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954.
8. Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Syntheses; VCH: Weinheim, 1997.
9. Corey, E. J.; Barnes-Seeman, D.; Lee, T. W.; Goodman, S. N. Tetrahedron Lett. 1997, 38, 6513-6516 and references therein.
10. (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
11. (b) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
12. (c) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
13. (d) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58.
14. (e) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559-7573.
15. (f) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786-787.
16. (g) Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1998, 120, 4895-4896.
17. (h) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649.
18. (a) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814-5815.
19. (b) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893-7894.
20. (c) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Connell, B. J. Am. Chem. Soc. 1999, 121, 669-685.
21. (d) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699.
22. For Sn(II)-box complexes as aldol catalysts see: (e) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859-10860.
23. (a) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868.
24. (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995.
25. Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595-598.
26. For two recent reviews on various aspects of chiral Cu(2+) Lewis acid-catalyzed processes see: (a) Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem, 1999, 71, 1407-1415. (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325-335.
27. For two recent reviews on various aspects of chiral Cu(2+) Lewis acid-catalyzed processes see: (a) Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem, 1999, 71, 1407-1415. (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325-335.
28. (a) Johannsen, M.; Jorgensen, K. A. J. Org. Chem. 1995, 60, 5757-5762.
29. (b) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165-2168.
30. (c) Johannsen, M.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 2 1997, 1183-1185.
31. During the course of this research two examples of Cu(II)-box catalyzed glyoxylate - ene reactions have appeared: (d) Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133-2143.
32. (e) Gethergood, N.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1999, 1869-1870.
33. A preliminary account of this work has appeared: Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay; S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825.
34. 2O-Cu-N-C dihedral angles are 30.0° and 36.0°. See: Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. C.; Woerpel, K. A. J. Org. Chem. 1998, 63, 4541-4544.
35. For chiral auxiliary based examples see: Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989-899.
36. A slower reaction and a reduced yield is observed when 4 is employed.
37. Due to the volatility of cis-butene, the reactions were performed in sealed tubes using glyoxylate as limiting reagent (see Supporting Information).
38. Barlett, P. A.; Tanzella, D. J.; Barstow, J. F. J. Org. Chem. 1982, 47, 3941.
39. For chiral auxiliary examples see: Whitesell, J. K.; Lawrence, R. M.; Chen, H.-H. J. Org. Chem. 1986, 51, 4779-4784.
40. Otera, J.; Niibo, Y.; Nozaki, H. Tetrahedron 1991, 47, 7625-7634.
41. Fluka 50% glyoxylate in toluene solution.
42. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815. For a review see: Sibi, M. P. Org. Prep. Proc. Int. 1993, 25, 15-40.
43. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815. For a review see: Sibi, M. P. Org. Prep. Proc. Int. 1993, 25, 15-40.
44. For a review on the use of azides see: Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297-368.
45. Thompson, A. S.; Humphrey, G. R.; DeMarco, A. M.; Mathre, D. J.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 5886-5888.
46. 2DPPA see: Shioiri, T.; Yamada, S.-I. Chem. Pharm. Bull. 1974, 22, 855-858.
47. 2DPPA see: Shioiri, T.; Yamada, S.-I. Chem. Pharm. Bull. 1974, 22, 855-858.
48. Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802. For a correction see: Whitesell, J. K.; Nabona, K.; Deyo, D. J. Org. Chem. 1989, 54, 2258. Reaction between N-glyoxyloyl- (2R)-borane-10,2-sultam and monosubstituted olefins has also been reported: Jezewski, A.; Chajewska, K.; Wielogórski, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 1741-1749.
49. Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802. For a correction see: Whitesell, J. K.; Nabona, K.; Deyo, D. J. Org. Chem. 1989, 54, 2258. Reaction between N-glyoxyloyl- (2R)-borane-10,2-sultam and monosubstituted olefins has also been reported: Jezewski, A.; Chajewska, K.; Wielogórski, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 1741-1749.
50. Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802. For a correction see: Whitesell, J. K.; Nabona, K.; Deyo, D. J. Org. Chem. 1989, 54, 2258. Reaction between N-glyoxyloyl-(2R)-borane-10,2-sultam and monosubstituted olefins has also been reported: Jezewski, A.; Chajewska, K.; Wielogórski, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 1741-1749.
51. Evans, D. A.; Burgey, C. S.; Korfowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699.
52. Due to the volatility of isobutylene, the reactions were performed in sealed tubes (see Supporting Information).
53. X-ray crystallography: (a) Reference 13. (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. T. J. Am. Chem. Soc. 1999, 121, 1994. Double stereodifferentiating experiments: (c) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. PM3 and EPR experiments: (d) Reference 8b,d.
54. X-ray crystallography: (a) Reference 13. (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. T. J. Am. Chem. Soc. 1999, 121, 1994. Double stereodifferentiating experiments: (c) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. PM3 and EPR experiments: (d) Reference 8b,d.
55. X-ray crystallography: (a) Reference 13. (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. T. J. Am. Chem. Soc. 1999, 121, 1994. Double stereodifferentiating experiments: (c) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. PM3 and EPR experiments: (d) Reference 8b,d.
56. X-ray crystallography: (a) Reference 13. (b) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. T. J. Am. Chem. Soc. 1999, 121, 1994. Double stereodifferentiating experiments: (c) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460. PM3 and EPR experiments: (d) Reference 8b,d.
57. Snider, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 2, pp 527-561.
58. (a) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757.
59. (b) Johannsen, M.; Yao, S.; Jørgensen, K. A. Chem. Commun. 1997, 2169.
60. (c) Johannsen, M.; Yao, S.; Graven, A.; Jørgensen, K. A. Pure Appl. Chem. 1998, 70, 1117.
61. (a) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879-2882.
62. (b) Reference 7h.
63. General Information is provided in the Supporting Information. The following are also contained in the Supporting Information: specific reaction conditions, characterization data, and absolute and relative stereochemical proofs.
64. (a) For the preparation of (S,S)-bis(tert-butyloxazoline) see: ref 14.
65. (b) For the preparation of (S,S)-bis(phenyloxazoline) see: Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728-9.
66. For the preparation of the Cu(II) complexes see: (c) ref 27 and (d) ref 14.
67. For the preparation of the Cu(II) complexes see: (c) ref 27 and (d) ref 14.