Catalytic, enantioselective, vinylogous aldol reactions

Angewandte Chemie - International Edition

Volumn 44, Issue 30, 2005, Pages 4682-4698

  Denmark, Scott E ^a   Heemstra Jr , John R ^a   Beutner, Gregory L ^a,b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Aldol reactions; Asymmetric catalysis; Dienol ethers; Regioselectivity; Vinylogy

Indexed keywords

ALDOL REACTIONS; FUNCTIONAL GROUPS; NATURAL PRODUCT SYNTHESIS; POLAR REACTIONS;

CHEMICAL BONDS; ETHERS; MOLECULES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALCOHOLS;

ALDEHYDE; ETHER DERIVATIVE; KETONE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; REVIEW; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ETHERS; KETONES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 23044486219     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462338     Document Type: Review

References (85)

1. For a recent review, see: J. Staunton, K. J. Weissman, Nat. Prod. Rep. 2001, 18, 380.
2. a) E. M. Carreira in Modern Carbonyl Chemistry, (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000, chap. 8;
3. b) E. M. Carreira in Comprehensive Asymmetric Catalysis, Vol. III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, chap. 29;
4. c) I. Paterson, C. J. Cowden, D. J. Wallace in Modern Carbonyl Chemistry (Ed.: I. Otera), Wiley-VCH, Weinheim, 2000, chap. 9;
5. d) E. M. Carreira in Catalytic Asymmetric Synthesis, 2nd Ed. (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, chap. 8B2;
6. e) M. Braun in Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), Vol. 3, Edition E21 (Eds.: G. Helmchen, R. Hoffman, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1996, p. 1603;
7. f) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357;
8. g) R. D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041;
9. h) T. Mukaiyama, S. Kobayashi, Org. React. 1994, 46, 1.
10. W. R. Roush, A. D. Palkowitz, K. Ando, J. Am. Chem. Soc. 1990, 112, 6348.
11. S. D. Rychnovsky, B. N. Rogers, T. I. Richardson, Acc. Chem. Res. 1998, 31, 9.
12. S. A. Burova, F. E. McDonald, J. Am. Chem. Soc. 2004, 126, 2495.
13. a) R. C. Fuson, Chem. Rev. 1935, 16, 1;
14. b) S. Krishnamurthy, J. Chem. Educ. 1982, 59, 543;
15. c) P. Bruneau, P. J. Taylor, A. J. Wilkinson, J. Chem. Soc. Perkin Trans. 2 1996, 2263.
16. A. M. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307.
17. A. Soriente, M. De Rosa, R. Villano, A. Scettri, Current Org. Chem. 2004, 8, 993.
18. J. L. Herrmann, G. R. Kieczykowski, R. H. Schlessinger, Tetrahedron Lett. 1973, 14, 2433.
19. M. W. Rathke, D. Sullivan, Tetrahedron Lett. 1972, 13, 4249.
20. T. Mukaiyama, A. Ishida, Chem. Lett. 1975, 319.
21. a) G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929;
22. b) J. Hassfeld, M. Kalesse, Synlett 2002, 2007;
23. c) M. Christmann, M. Kalesse, Tetrahedron Lett. 2001, 42, 1269;
24. d) X. Moreau, J.-M. Campagne, Tetrahedron Lett. 2001, 42, 4467;
25. e) G. Rassu, P. Carta, L. Pinna, L. Battistini, F. Zanardi, D. Acquotti, G. Casiraghi, Eur. J. Org. Chem. 1999, 1395;
26. f) B. Dudot, L. Micouin, I. Baussanne, J. Royer, Synthesis 1999, 688;
27. g) P. Spanu, G. Rassu, L. Pinna, L. Battistini, G. Casiraghi, Tetrahedron: Asymmetry 1997, 8, 3237;
28. h) C. W. Jefford, D. Jaggi, J. Boukouvalas, Tetrahedron Lett. 1987, 28, 4037;
29. i) H.-F. Chow, I. Fleming, Tetrahedron Lett. 1985, 26, 397.
30. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley-Interscience, New York, 1996, p. 45.
31. K. Fukui, T. Yonezawa, C. Nagata, H. Shingu, J. Chem. Phys. 1954, 22, 1433.
32. The ground-state conformations of the dienolates and dienol ethers were found by using the PC GAMESS version of GAMESS (US) QC package at the STO-3G(p,d)** level. The orbital analysis, HOMO-coefficient data (C.O.), and electrophilic susceptibility (E.S.) were then calculated from these structures by using density functional theory at the B88-LYP level with the CAChe program. a) A. A. Granovsky, http://classic.chem.msu.su/gran/gamess/index. html;
33. b) M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. J. Jensen, S. Koseki, N. Matsuriaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347;
34. c) CAChe WorkSystem Pro, Version 6.1.10, 2004, CAChe Group, Fujitsu America, Inc., Beaverton, OR.
35. R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12 360.
36. a) K. Furuta, T. Maruyama, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 1041;
37. b) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481.
38. M. Sato, S. Sunami, Y. Sugita, C. Kaneko, Chem. Pharm. Bull 1994, 42, 839.
39. S.-I. Kiyooka, M. A. Hena, T. Yabukami, K. Murai, F. Goto, Tetrahedron Lett. 2000, 41, 7511.
40. S.-I. Kiyooka, M. A. Hena, J. Org. Chem. 1999, 64, 5511.
41. K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 1993, 115, 7039.
42. M. Sato, S. Sunami, Y. Sugita, C. Kaneko, Heterocycles 1995, 41, 1435.
43. a) M. De Rosa, M. R. Acocella, R. Villano, A. Soriente, A. Scettri, Tetrahedron: Asymmetry 2003, 14, 2499;
44. b) M. De Rosa, M. R. Acocella, R. Villano, A. Soriente, A. Scettri, Tetrahedron Lett. 2003, 44, 6087;
45. c) R. Villano, M. De Rosa, C. Salerno, A. Soriente, A. Scettri, Tetrahedron: Asymmetry 2002, 13, 1949;
46. d) M. De Rosa, M. R. Acocella, A. Soriente, A. Scettri, Tetrahedron: Asymmetry 2001, 12, 1529;
47. e) M. De Rosa, A. Soriente, A. Scettri, Tetrahedron: Asymmetry 2000, 11, 3187;
48. f) A. Soriente, M. De Rosa, A. Apicella, A. Scettri, G. Sodano, Tetrahedron: Asymmetry 1999, 10, 4481;
49. g) M. De Rosa, R. Dell'Aglio, A. Soriente, A. Scettri, Tetrahedron: Asymmetry 1999, 10, 3659;
50. h) A. Soriente, M. De Rosa, P. Dovinola, G. Sodano, A. Scettri, Tetrahedron: Asymmetry 1998, 9, 2197.
51. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088;
52. Angew. Chem. Int. Ed. 1998, 37, 2923.
53. a) R. Villano, M. R. Acocella, M. De Rosa, M. A. Soriente, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 2421;
54. b) A. Soriente, M. De Rosa, M. Stanzione, R. Villano, A. Scettri, Tetrahedron: Asymmetry 2001, 12, 959;
55. c) A. Soriente, M. De Rosa, R. Villano, A. Scettri, Tetrahedron: Asymmetry 2000, 11, 2255.
56. Y. Kim, R. A. Singer, E. M. Carreira, Angew. Chem. 1998, 110, 1321;
57. Angew. Chem. Int. Ed. 1998, 37, 1261.
58. S. Anne, W. Yong, M. Vandewalle, Synlett, 1999, 1435.
59. a) D. A. Evans, M. C. Kozlowski, J. A. Murry, C. S. Burgey, K. R. Campos, B. T. Connell, R. J. Staples, J. Am. Chem. Soc. 1999, 121, 669;
60. b) D. A. Evans, J. A. Murry, M. C. Kozlowski, J. Am. Chem. Soc. 1996, 118, 5814.
61. D. A. Evans, D. M. Fitch, T. E. Smith, V. J. Cee, J. Am. Chem. Soc. 2000, 122, 10 033.
62. D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, M. Lautens, J. Am. Chem. Soc. 1999, 121, 7540.
63. Y. Shimada, Y. Matsuoka, R. Irie, T. Katsuki, Synlett 2004, 57.
64. S. E. Denmark, G. L. Beutner, J. Am. Chem. Soc. 2003, 125, 7800.
65. a) B. L. Pagenkopf, J. Krüger, A. Stojanovic, E. M. Carreira, Angew. Chem. 1998, 110, 3312;
66. Angew. Chem. Int. Ed. 1998, 37, 3124;
67. b) J. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837.
68. A. Fettes, E. M. Carreira, Angew. Chem. 2002, 114, 4272;
69. Angew. Chem. Int. Ed. 2002, 41, 4098.
70. B. B. Snider, F. Song, Org. Lett. 2001, 3, 1817.
71. C. J. Brennan, J.-M. Campagne, Tetrahedron Lett. 2001, 42, 5195.
72. J. Krüger, E. M. Carreira, Tetrahedron Lett. 1998, 39, 7013.
73. 4/(R)-binol complex was reported; the adducts were afforded in yields of 26-98% with d.r.(syn/anti) = 79:21-87:13 and e.r.(1′R,2′R/1′S,2′S) = 93.0:7.0-99.5:0.5; M. De Rosa, M. R. Acocella, M. F. Rega, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 3029.
74. G. Bluet, J.-M. Campagne, Tetrahedron Lett. 1999, 40, 5507.
75. I. Paterson, R. D. M. Davies, A. C. Heinmann, R. Marquez, A. Meyer, Org. Lett. 2003, 5, 4477.
76. D. A. Evans, E. Hu, J. D. Burch, G. Jaeschke, J. Am. Chem. Soc. 2002, 124, 5654.
77. G. Bluet, J.-M. Campagne, J. Org. Chem. 2001, 66, 4293.
78. G. Bluet, B. Bazan-Tejeda, J.-M. Campagne, Org. Lett. 2001, 3, 3807.
79. S. E. Denmark, T. Wynn, G. L. Beutner, J. Am. Chem. Soc. 2002, 124, 13 405.
80. a) M. Szlosek, B. Figadère, Angew. Chem. 2000, 112, 1869;
81. Angew. Chem. Int. Ed. 2000, 39, 1799;
82. b) M. Szlosek, X. Franck, B. Figadère, A. Cavé, J. Org. Chem. 1998, 63, 5169.
83. a) S. Onitsuka, Y. Matsuoka, R. Irie, T. Katsuki, Chem. Lett. 2003, 32, 974;
84. b) Y. Matsuoka, R. Irie, T. Katsuki, Chem. Lett. 2003, 32, 584.
85. S. E. Denmark, J. R. Heemstra, Jr., Synlett 2004, 2411.