(Diisopinocampheyl)borane-mediated reductive aldol reactions of acrylate esters: Enantioselective synthesis of anti-aldols

Organic Letters

Volumn 15, Issue 15, 2013, Pages 3922-3925

  Allais, Christophe ^a   Nuhant, Philippe ^a   Roush, William R ^a  

^a Scripps Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(DIISOPINOCAMPHEYL)BORANE; 3-HYDROXYBUTANAL; ACRYLIC ACID; ACRYLIC ACID DERIVATIVE; ALDEHYDE; ALDOL; BORANE DERIVATIVE; ESTER;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ACRYLATES; ALDEHYDES; BORANES; CATALYSIS; ESTERS; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84881255675     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401679g     Document Type: Article

References (70)

1. Heathcock, C. H. Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: New York, 1991; Vol. 2, p 181.
2. Kim, B. M.; Williams, S. F.; Masamune, S. Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: New York, 1991; Vol. 2, p 239.
3. Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1
4. Arya, P.; Qin, H. Tetrahedron 2000, 56, 917-947
5. Mahrwald, R. Modern Aldol Reactions; Wiley-VCH: Weinheim, Germany, 2004.
6. Denmark, S. E.; Fiujimori, S. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: 2004; Vol. 2, pp 229-326.
7. Shibasaki, M.; Matsunaga, S.; Kumagai, N. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: 2004; Vol. 2, pp 197-227.
8. Johnson, J. S.; Nicewicz, D. A. In Modern Aldol Reactions; Rainer, M., Ed.; Wiley VCH: 2006; Vol. 2, pp 69-103.
9. Geary, L. M.; Hultin, P. G. Tetrahedron: Asymmetry 2009, 20, 131-173
10. Bisai, V.; Bisai, A.; Singh, V. K. Tetrahedron 2012, 68, 4541-4580
11. Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354-366
12. Nishiyama, H.; Shiomi, T. Top. Curr. Chem. 2007, 279, 105-137
13. Han, S. B.; Hassan, A.; Krische, M. J. Synthesis 2008, 17, 2669-2679
14. Garner, S. A.; Han, S. B.; Krische, M. J. In Modern Reduction Methods; Andersson, P. G.; Munslow, I. J., Eds.; Wiley-VCH: Weinheim, 2008; pp 387-417.
15. Danda, H.; Hansen, M. M.; Heathcock, C. H. J. Org. Chem. 1990, 55, 173-181
16. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747-5750
17. Oppolzer, W.; Starkemann, C.; Rodriguez, I.; Bernardinelli, G. Tetrahedron Lett. 1991, 32, 61-64
18. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321-4324
19. Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586-2587
20. Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 4387-4388
21. Kurosu, M.; Lorca, M. J. Org. Chem. 2001, 66, 1205-1209
22. Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393
23. Crimmins, M. T.; McDougall, P. J. Org. Lett. 2003, 5, 591-594
24. Ghosh, A. K.; Kim, J.-H. Org. Lett. 2003, 5, 1063-1066
25. Hajra, S.; Giri, A. K.; Karmakar, A.; Khatua, S. Chem. Commun. 2007, 2408-2410
26. Fanjul, S.; Hulme, A. N. J. Org. Chem. 2008, 73, 9788-9791
27. Dai, W.-M.; Feng, G.; Wu, J.; Sun, L. Synlett 2008, 7, 1013-1016
28. Shinisha, C. B.; Sunoj, R. B. Org. Lett. 2010, 12, 2868-2871
29. May, A.; Connell, N.; Dahlmann, H.; Hoye, T. Synlett 2010, 13, 1984-1986
30. Grimster, N. P.; Wilton, D. A. A.; Chan, L. K. M.; Godfrey, C. R. A.; Green, C.; Owen, D. R.; Gaunt, M. J. Tetrahedron 2010, 66, 6429-6436
31. Li, Y.-J.; Hung, H.-Y.; Liu, Y.-W.; Lin, P.-J.; Huang, H.-J. Tetrahedron 2011, 67, 927-935
32. Chouhan, M.; Sharma, R.; Nair, V. A. Org. Lett. 2012, 14, 5672-5675
33. Meyers, A. I.; Yamamoto, Y. J. Am. Chem. Soc. 1981, 103, 4278-4279
34. Masamune, S.; Sato, T.; Kim, B.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281
35. Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedron Lett. 1989, 30, 7121-7124
36. Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976-4977
37. Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732
38. Denmark, S. E.; Wynn, T.; Beutner, G. L. J. Am. Chem. Soc. 2002, 124, 13405-13407
39. Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292-3302
40. Jung, M. E.; Zhang, T. Org. Lett. 2008, 10, 137-140
41. Díaz-Oltra, S.; Ruiz, P.; Falomir, E.; Murga, J.; Carda, M.; Marco, J. A. Org. Biomol. Chem. 2012, 10, 6937-6944
42. Sureshkumar, D.; Kawato, Y.; Iwata, M.; Kumagai, N.; Shibasaki, M. Org. Lett. 2012, 14, 3108-3111
43. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799
44. Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541-3544
45. Yang, H.; Mahapatra, S.; Cheong, P. H.-Y.; Carter, R. G. J. Org. Chem. 2010, 75, 7279-7290
46. Li, S.; Wu, C.; Fu, X.; Miao, Q. Ind. Eng. Chem. Res. 2011, 50, 13711-13716
47. Nishiyama, H.; Shiomi, T.; Tsuchiya, Y.; Matsuda, I. J. Am. Chem. Soc. 2005, 127, 6972-6973
48. Ito, J.; Shiomi, T.; Nishiyama, H. Adv. Synth. Catal. 2006, 348, 1235-1240
49. Shiomi, T.; Ito, J.; Yamamoto, Y.; Nishiyama, H. Eur. J. Org. Chem. 2006, 5594-5600
50. Hashimoto, T.; Ito, J.; Nishiyama, H. Tetrahedron 2008, 64, 9408-9412
51. Shiomi, T.; Adachi, T.; Ito, J.; Nishiyama, H. Org. Lett. 2009, 11, 1011-1014
52. Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5678-5680
53. Boldrini, G. P.; Mancini, F.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1990, 1680-1681
54. Boldrini, G. P.; Bortolotti, M.; Mancini, F.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1991, 56, 5820-5826
55. Matsumoto, Y.; Hayashi, T. Synlett 1991, 349-350
56. Huddleston, R. R.; Cauble, D. F.; Krische, M. J. J. Org. Chem. 2003, 68, 11-14
57. Ghosh, A. K.; Kass, J.; Anderson, D. D.; Xu, X.; Marian, C. Org. Lett. 2008, 10, 4811-4814
58. Nuhant, P.; Allais, C.; Roush, W. R. Angew. Chem., Int. Ed. 2013, 52, in press (doi: 10.1002/anie.201302535).
59. Corey, E. J.; Lee, D.-H. Tetrahedron Lett. 1993, 34, 1737-1740
60. Brown, H. C.; Singaram, B. J. Org. Chem. 1984, 49, 945-947
61. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519
62. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096
63. (Ramachandran, P. V.; Pratihar, D. Org. Lett. 2009, 11, 1467-1470).
64. Goodman, J. M.; Paton, R. S. Chem. Commun. 2007, 2124-2126
65. Paterson, I.; Goodman, J. M. Tetrahedron Lett. 1989, 30, 997-1000
66. Paterson, I.; Goodman, J. M.; Anne Lister, M.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663-4684
67. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945-948
68. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. 1985, 24, 1-30
69. Nuhant, P.; Kister, J.; Lira, R.; Sorg, A.; Roush, W. R. Tetrahedron 2011, 67, 6497-6512
70. Lira, R.; Roush, W. R. Org. Lett. 2007, 9, 4315-4318