Design and enantioselective synthesis of Cashmeran odorants by using "enol catalysis

Angewandte Chemie - International Edition

Volumn 54, Issue 6, 2015, Pages 1960-1964

  Felker, Irene ^a   Pupo, Gabriele ^b   Kraft, Philip ^a   List, Benjamin ^b  

^a GIVAUDAN SCHWEIZ AG   (Switzerland)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Br nsted acid catalysis; Enol catalysis; Fragrances; Michael addition; Structure activity relationships

Indexed keywords

ADDITION REACTIONS; ENANTIOSELECTIVITY; FRAGRANCES; KETONES; ODORS;

ACID CATALYSIS; CYCLIC KETONES; ENANTIOPURE; ENANTIOSELECTIVE SYNTHESIS; HIGH ENANTIOSELECTIVITY; MICHAEL ADDITIONS; QUATERNARY STEREOCENTERS; STRUCTURE ACTIVITY RELATIONSHIPS;

CATALYSIS;

EID: 84922057979     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409591     Document Type: Article

References (86)

1. a) J. B. Hall, E. T. Theimer (IFF), Ger. Offen. DE 2036936A, 1971 [Chem. Abst. 1971, 75, 109957]
2. th ed., Wiley-VCH, Weinheim, 2006, p. 92.
3. P. Kraft, V. Di Cristofaro, S. Jordi, Chem. Biodiversity 2014, 11, 1567-1596.
4. Molecular Operating Environment (MOE) Release 2013.0801-fully integrated drug discovery software package, Chemical Computing Group, Montreal, Quebec, Canada H3A 2R7, 2013.http://www.chemcomp.com/.
5. P. Kraft, S. Jordi, N. Denizot, I. Felker, Eur. J. Org. Chem. 2014, 554-563.
6. a) M. Pfau, G. Revial, A. Guingant, J. d'Angelo, J. Am. Chem. Soc. 1985, 107, 273-274
7. b) T. Volpe, G. Revial, M. Pfau, J. d'Angelo, Tetrahedron Lett. 1987, 28, 2367-2370
8. c) J. d'Angelo, D. Desmaële, F. Dumas, A. Guingant, Tetrahedron: Asymmetry 1992, 3, 459-505
9. d) M. Pfau, I. Jabin, G. Revial, J. Chem. Soc. Perkin Trans. 1 1993, 1935-1936
10. e) I. Jabin, G. Revial, A. Tomas, P. Lemoine, M. Pfau, Tetrahedron: Asymmetry 1995, 6, 1795-1812
11. f) C. Cavé, D. Desmaële, J. d'Angelo, C. Riche, A. Chiaroni, J. Org. Chem. 1996, 61, 4361-4368
12. g) C. Camara, D. Joseph, F. Dumas, J. d'Angelo, A. Chiaroni, Tetrahedron Lett. 2002, 43, 1445-1448
13. D. Desmaële, S. Delarue-Cochin, C. Cavé, J. d'Angelo, G. Morgant, Org. Lett. 2004, 6, 2421-2424.
14. J. Y. Kang, R. G. Carter, Org. Lett. 2012, 14, 3178-3181.
15. a) T. Hayashi, K. Kanehira, T. Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113-120
16. b) B. M. Trost, X. Ariza, Angew. Chem. Int. Ed. Engl. 1997, 36, 2635-2637
17. Angew. Chem. 1997, 109, 2749-2751
18. c) B. M. Trost, R. Radinov, E. M. Grenzer, J. Am. Chem. Soc. 1997, 119, 7879-7880
19. d) B. M. Trost, G. M. Schroeder, Chem. Eur. J. 2005, 11, 174-184
20. e) X. X. Yan, C. G. Liang, Y. Zhang, W. Hong, B. X. Cao, L. X. Dai, X. L. Hou, Angew. Chem. Int. Ed. 2005, 44, 6544-6546
21. Angew. Chem. 2005, 117, 6702-6704
22. f) S. L. You, X. L. Hou, L. X. Dai, B. X. Cao, J. Sun, Chem. Commun. 2000, 1933-1934
23. g) S. L. You, X. L. Hou, L. X. Dai, X. Z. Zhu, Org. Lett. 2001, 3, 149-151
24. h) R. Kuwano, K. Uchida, Y. Ito, Org. Lett. 2003, 5, 2177-2179.
25. a) J. Christoffers, A. Mann, Chem. Eur. J. 2001, 7, 1014-1027
26. b) J. Christoffers, A. Baro, Angew. Chem. Int. Ed. 2003, 42, 1688-1690
27. Angew. Chem. 2003, 115, 1726-1728
28. J. Christoffers, A. Mann, Angew. Chem. Int. Ed. 2001, 40, 4591-4597
29. Angew. Chem. 2001, 113, 4725-4732
30. J. Christoffers, G. Koripelly, A. Rosiak, M. Rossle, Synthesis 2007, 1279-1300.
31. a) J. Tsuji, I. Minami, I. Shimizu, Tetrahedron Lett. 1983, 24, 1793-1796
32. b) J. Tsuji, I. Minami, Acc. Chem. Res. 1987, 20, 140-145.
33. a) D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 15044-15045
34. b) J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. Int. Ed. 2005, 44, 6924-6927
35. Angew. Chem. 2005, 117, 7084-7087
36. c) C. M. Reeves, D. C. Behenna, B. M. Stoltz, Org. Lett. 2014, 16, 2314-2317
37. d) C. M. Reeves, C. Eidamshaus, J. Kim, B. M. Stoltz, Angew. Chem. Int. Ed. 2013, 52, 6718-6721
38. Angew. Chem. 2013, 125, 6850-6853
39. e) J. Streuff, D. E. White, S. C. Virgil, B. M. Stoltz, Nat. Chem. 2010, 2, 192-196.
40. a) J. D. Weaver, A. Recio, A. J. Grenning, J. A. Tunge, Chem. Rev. 2011, 111, 1846-1913
41. b) A. Y. Hong, B. M. Stoltz, Eur. J. Org. Chem. 2013, 2745-2759.
42. a) T. Ooi, K. Maruoka, Angew. Chem. Int. Ed. 2007, 46, 4222-4266
43. Angew. Chem. 2007, 119, 4300-4345
44. b) S. Shirakawa, K. Maruoka, Angew. Chem. Int. Ed. 2013, 52, 4312-4348
45. Angew. Chem. 2013, 125, 4408-4445.
46. a) G. Bartoli, M. Bosco, A. Carlone, A. Cavalli, M. Locatelli, A. Mazzanti, P. Ricci, L. Sambri, P. Melchiorre, Angew. Chem. Int. Ed. 2006, 45, 4966-4970
47. Angew. Chem. 2006, 118, 5088-5092
48. b) M. Capuzzi, D. Perdicchia, K. A. Jorgensen, Chem. Eur. J. 2008, 14, 128 - 135;
49. c) M. Bella, T. Gasperi, Synthesis 2009, 1583-1614.
50. a) B. List, I. Coric, O. O. Grygorenko, P. S. Kaib, I. Komarov, A. Lee, M. Leutzsch, S. Chandra Pan, A. V. Tymtsunik, M. van Gemmeren, Angew. Chem. Int. Ed. 2014, 53, 282-285
51. Angew. Chem. 2014, 126, 286-289
52. b) E. Arceo, I. D. Jurberg, A. Alvarez-Fernandez, P. Melchiorre, Nat. Chem. 2013, 5, 750-756.
53. a) R. M. Pollack, Bioorg. Chem. 2004, 32, 341-353
54. b) S. D. Fried, S. G. Boxer, J. Phys. Chem. B 2012, 116, 690-697
55. c) J. A. Gerlt, P. G. Gassman, J. Am. Chem. Soc. 1992, 114, 5928-5934.
56. a) P. D. Bartlett, C. H. Stauffer, J. Am. Chem. Soc. 1935, 57, 2580-2583
57. b) C. Rappe, W. H. Sachs, J. Org. Chem. 1967, 32, 3700-3703
58. c) G. E. Lienhard, T. C. Wang, J. Am. Chem. Soc. 1969, 91, 1146-1153
59. d) J. R. Keeffe, A. J. Kresge, J. Toullec, Can. J. Chem. 1986, 64, 1224-1227.
60. a) D. Kampen, C. M. Reisinger, B. List, Top. Curr. Chem. 2010, 291, 395-456
61. b) R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603-614
62. c) M. Terada, Synthesis 2010, 1929-1982
63. d) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010.
64. a) S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. Int. Ed. 2005, 44, 7424-7427
65. Angew. Chem. 2005, 117, 7590-7593
66. b) G. Adair, S. Mukherjee, B. List, Aldrichimica Acta 2008, 41, 31-39
67. c) M. Klussmann, L. Ratjen, S. Hoffmann, V. Wakchaure, R. Goddard, B. List, Synlett 2010, 2189-2192.
68. a) T. Akiyama, T. Katoh, K. Mori, Angew. Chem. Int. Ed. 2009, 48, 4226 - 4228;
69. Angew. Chem. 2009, 121, 4290-4292
70. b) M. Yamanaka, M. Hoshino, T. Katoh, K. Mori, T. Akiyama, Eur. J. Org. Chem. 2012, 4508-4514.
71. G. Pousse, F. Le Cavelier, L. Humphreys, J. Rouden, J. Blanchet, Org. Lett. 2010, 12, 3582-3585.
72. M. van Gemmeren, F. Lay, B. List, Aldrichimica Acta 2014, 47, 3-13.
73. CCDC 1031803 [(S)-5a] and 1031804 [(R)-9] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
74. a) J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524
75. b) D. Lenoir, Synthesis 1989, 883-897.
76. D. Lenoir, Synthesis 1977, 553-554.
77. a) G. Stork, K. Zhao, Tetrahedron Lett. 1989, 30, 287-290
78. b) V. M. T. Carneiro, H. M. C. Ferraz, T. O. Vieira, E. E. Ishikawa, L. F. Silva, Jr., J. Org. Chem. 2010, 75, 2877-2882.
79. a) K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2245-2258
80. b) K. C. Nicolaou, T. Montagnon, P. S. Baran, Angew. Chem. Int. Ed. 2002, 41, 1386-1389
81. Angew. Chem. 2002, 114, 1444-1447
82. c) M. Uyanik, M. Akakura, K. Ishihara, J. Am. Chem. Soc. 2009, 131, 251-262
83. d) D. Walker, J. D. Hiebert, Chem. Rev. 1967, 67, 153-195
84. F. J. Aladro, F. M. Guerra, F. J. Moreno-Dorado, J. M. Bustamante, Z. D. Jorge, G. M. Massanet, Tetrahedron 2001, 57, 2171-2178
85. e) T. Diao, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 14566-14569.
86. Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013.