The development of the asymmetric Morita-Baylis-Hillman reaction catalyzed by chiral Brønsted acids

Advanced Synthesis and Catalysis

Volumn 346, Issue 9-10, 2004, Pages 1231-1240

  McDougal, Nolan T ^a   Trevellini, Whitney L ^a   Rodgen, Stacy A ^a   Kliman, Laura T ^a   Schaus, Scott E ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Br nsted acid; Morita Baylis Hillman reaction; Organic catalysis; Phosphanes

Indexed keywords

ACID; ALDEHYDE; CYCLOHEXANONE; LEWIS ACID; NAPHTHOL DERIVATIVE; PHOSPHONIUM DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; BAYLIS HILLMAN REACTION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HYDROGEN BOND; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 5144219609     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404122     Document Type: Article

References (64)

1. a) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-891;
2. b) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052;
3. c) E. Ciganek, in: Organic Reactions, Vol. 51, (Ed.: L. A. Paquette), Wiley, NewYork, 1997, pp. 201-350;
4. d) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001-8062;
5. e) S. E. Drewes, G. H. P. Roos, Tetrahedron 1988, 44, 4653-4670.
6. A. B. Baylis, M. E. D. Hillman, (Celanese Corp.), Ger. Offen. 2,155,113, 1972; Chem. Abstr. 1972, 77, 34,174q.
7. R. Oda, T. Kawabata, S. Tanimoto, Tetrahedron Lett. 1964, 5, 1653-1657.
8. K. Morita, Z. Suzuki, H. Hirose, Bull. Chem. Soc. Jpn. 1968, 41, 2815.
9. a) S. Rafel, J. W. Leahy, J. Org. Chem. 1997, 62, 1521-1522;
10. b) S. E. Drewes, M. B. Rohwer, Synthetic Commun. 1997, 27, 415-424.
11. L. J. Brzezinski, S. Rafel, J. W. Leahy, J. Am. Chem. Soc. 1997, 119, 4317-4318.
12. a) W. Oppolzer, Pure Appl. Chem. 1990, 62, 1241-1250;
13. b) B. H. Kim, D. P. Curran, Tetrahedron 1993, 49, 293-318;
14. c) W. Oppolzer, Tetrahedron 1987, 43, 1969-2004;
15. d) W. Oppolzer, Pure Appl. Chem. 1988, 60, 39-48.
16. K.-S. Yang, K. Chen, Org. Lett. 2000, 2, 729-731.
17. V. K. Aggarwal, A. Mereu, G. J. Tarver, R. McCague, J. Org Chem. 1998, 63, 7183-7189.
18. K.-S. Yang, W.-D. Lee, J.-F. Pan, K. Chen, J. Org. Chem. 2003, 68, 915-919.
19. Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219-10220.
20. a) M. Shi, J.-K. Jiang, Tetrahedron: Asymmetry 2002, 13, 1941-1947;
21. b) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510.
22. Y. Iwabuchi, M. Furukawa, T. Esumi, S. Hatakeyama, Chem. Commun. 2001, 2030-2031.
23. J. E. Imbriglio, M. M. Vasbinder, S. J. Miller, Org. Lett. 2003, 5, 3741-3743.
24. For the use of water as H-bond donor, see: a) J. Augé, N. Lubin, A. Lubineau, Tetrahedron Lett. 1994, 35, 7947-7948; b) C. Yu, B. Liu, L. Hu, J. Org. Chem. 2001, 66, 5413-5418; c) V. K. Aggarwal, D. K. Dean, A. Mereu, R. Williams, J. Org. Chem. 2002, 67, 510-514;
25. For the use of water as H-bond donor, see: a) J. Augé, N. Lubin, A. Lubineau, Tetrahedron Lett. 1994, 35, 7947-7948; b) C. Yu, B. Liu, L. Hu, J. Org. Chem. 2001, 66, 5413-5418; c) V. K. Aggarwal, D. K. Dean, A. Mereu, R. Williams, J. Org. Chem. 2002, 67, 510-514;
26. For the use of water as H-bond donor, see: a) J. Augé, N. Lubin, A. Lubineau, Tetrahedron Lett. 1994, 35, 7947-7948; b) C. Yu, B. Liu, L. Hu, J. Org. Chem. 2001, 66, 5413-5418; c) V. K. Aggarwal, D. K. Dean, A. Mereu, R. Williams, J. Org. Chem. 2002, 67, 510-514;
27. for the use of alcoholic solvents, see: d) F. Ameer, S. E. Drewes, S. Freese, P. T. Kaye, Synth. Commun. 1988, 18, 495-500;
28. for the use of 3-hydroxyquinuclidine, see: e) S. E. Drewes, S. D. Freese, N. D. Emslie, G. H. P. Roos, Synth. Commun. 1988, 18, 1565-1572.
29. K. Oohashi, S. Ido, (Osaka Juki Kagaku Kogyo Kk, Jpn.), Jpn. Kokai Tokkyo Kohu (Japanese Patent) 05 17,375, 1993; Chem. Abstr. 1993, 118, 254,552 s.
30. Y. M. A. Yamada, S. Ikegami, Tetrahedron Lett. 2000, 41, 2165-2169.
31. S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
32. A preliminary report of these results has been communicated: N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc. 2003, 125, 12094-12095.
33. R. R. Schrock, J. Y. Jamieson, S. J. Dolman, S. A. Miller, P. J. Bonitatebus Jr., A. H. Hoveyda, Organometallics, 2002, 21, 409-417.
34. J. Long, J. Hu, X. Shen, B. Ji, K. Ding, J. Am. Chem. Soc. 2002, 124, 10-11.
35. D. J. Cram, R. C. Helgeson, S. C. Peacock, L. J. Kaplan, L. A. Domeier, P. Moreau, K. Koga, J. M. Mayer, Y. Chao, M. G. Siegel, D. H. Hoffman, G. D. Y. Sogah, J. Org. Chem. 1978, 43, 1930-1946.
36. A. K. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028.
37. B. I. Alo, A. Kandil, P. A. Patil, M. J. Sharp, M. A. Siddiqui, V. Snieckus, J. Org. Chem. 1991, 56, 3763-3768.
38. 3 solution, rather than water, in order to quench the formation of HBr in the reaction mixture (see experimental section).
39. a) A. N. Thadali, A. R. Stankovic, V. H. Rawal, Proc. Natl. Acad. Sci. USA 2004, 101, 5846-5850;
40. b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357;
41. c) G. D. Joly, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 4102-4103;
42. d) B. M. Nugent, R. A. Yoder, J. N. Johnston, J. Am. Chem. Soc. 2004, 126, 3418-3419;
43. e) S. Kobayashi, C. Ogawa, H. Konishi, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 6610-6611;
44. f) Z. Tang, F. Jiang, L.-T. Yu, X. Cui, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Y.-D. Wu, J. Am. Chem. Soc. 2003, 125, 5262-5263;
45. g) M., Harmata, S. K. Ghosh, X. Hong, S. Wacharasindhu, P. Kirchhoefer, J. Am. Chem. Soc. 2003, 125, 2058-2059;
46. h) S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192-1194;
47. i) K. Juhl, K. A. Jørgensen, Angew. Chem. Int. Ed. 2003, 42, 1498-1501;
48. j) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. Int. Ed. 2003, 42, 661-665;
49. k) Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146;
50. l) A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964-12965;
51. m) M. S. Kerr, J. R. de Alaniz, T. Rovis, J. Am. Chem. Soc. 2002, 124, 10298-10299;
52. n) P. Vachal, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012-10014;
53. o) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894-7895;
54. p) S.-K. Tian, L. Deng, J. Am. Chem. Soc. 2001, 123, 6195-6196;
55. q) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370-4371;
56. r) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875;
57. s) A. E. Taggi, A. M. Hafez, H. Wack, B. Young, W. J. Drury III, T. Lectka, J. Am. Chem. Soc. 2000, 122, 7831-7832;
58. t) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244;
59. u) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396;
60. v) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621.
61. C. M. Marson, D. W. M. Benzies, A. D. Hobson, Tetrahedron 1991, 47, 5491-5506.
62. T. Kataoka, T. Iwama, S.-I. Tsujiyama, T. Iwamura, S.-I. Watanabe, Tetrahedron, 1998, 54, 11813-11824.
63. M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298.
64. M. Nakajima, I. Miyoshi, K. Kanayama, S.-I. Hashimoto, M. Noji, K. Koga, J. Org. Chem. 1999, 64, 2264-2271.