(2 S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-catalyzed efficient stereoselective michael addition of cyclohexanone and cyclopentanone to nitroolefins

Synthesis (Germany)

Volumn 45, Issue 10, 2013, Pages 1406-1413

  Singh, Kamalnain ^a   Singh, Paramjit ^a   Kaur, Amarjit ^a   Singh, Pushpinder ^a   Sharma, Sandeepkumar ^a   Khullar, Sadhika ^b   Mandal, Sanjay K ^b  

^a PANJAB UNIVERSITY   (India)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH MOHALI   (India)

Author keywords

amino sulfoxide; ketones; Michael addition reaction; nitroolefins; organocatalyst

Indexed keywords

AMINO SULFOXIDE; CYCLOHEXANONES; CYCLOPENTANONE; MICHAEL ADDITION REACTIONS; MICHAEL ADDITIONS; NITROOLEFINS; ORGANOCATALYSTS; STEREO-SELECTIVE;

ADDITION REACTIONS; KETONES; STEREOSELECTIVITY;

BIOCATALYSTS;

2 (2 NITRO 1 PHENYLETHYL)CYCLOHEXANONE; 2 [(PHENYLSULFINYL)METHYL]PYRROLIDINE; 2 [1 (1 NAPHTHYL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (1,3 BENZODIOXOL 5 YL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (2 CHLOROPHENYL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (3 CHLOROPHENYL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (3 METHOXYPHENYL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (3,4 DIMETHOXYPHENYL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (4 CHLOROPHENYL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (4 ETHOXY 3 METHOXYPHENYL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (4 METHOXYPHENYL) 2 NITROETHYL]CYCLOHEXANONE; 2 [1 (FURAN 2 YL) 2 NITROETHYL]CYCLOHEXANONE; 2 [2 NITRO 1 (3 NITROPHENYL)ETHYL]CYCLOHEXANONE; 3 METHYL 5 NITRO 4 PHENYLPENTAN 2 ONE; 4 (4 CHLOROPHENYL) 5 NITROPENTAN 2 ONE; 4 METHYL 6 NITRO 5 PHENYLHEXAN 3 ONE; ALKENE DERIVATIVE; CYCLOALKANONE; CYCLOHEXANONE; CYCLOPENTANONE DERIVATIVE; NITROOLEFIN DERIVATIVE; PYRROLIDINE DERIVATIVE; TERT BUTYL 2 (HYDROXYMETHYL)PYRROLIDINE 1 CARBOXYLIC ACID; TERT BUTYL 2 [(PHENYLSULFANYL)METHYL]PYRROLIDINE 1 CARBOXYLIC ACID; TERT BUTYL 2 [(PHENYLSULFINYL)METHYL]PYRROLIDINE 1 CARBOXYLIC ACID; TERT BUTYL 2 [(TOSYLOXY)METHYL]PYRROLIDINE 1 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84877583643     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316917     Document Type: Article

References (71)

1. Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138.
2. Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
3. List, B.; Yang, J. W. Science (Washington, D.C.) 2006, 313, 1584.
4. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem. Int. Ed. 2007, 46, 1570.
5. Gaunt, M. J.; Johansson, C. C. C.; McNally, A.; Vo, N. T. Drug Discovery Today 2007, 12, 8.
6. Pellissier, H. Tetrahedron 2007, 63, 9267.
7. MacMillan, D. W. C. Nature (London) 2008, 455, 304.
8. Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638.
9. Bertelsen, S.; Jorgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178.
10. Enders, D.; Wang, C.; Liebich, J. X. Chem. Eur. J. 2009, 15, 11058. For reviews on organocatalytic asymmetric conjugate addition reactions
11. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
12. Christoffers, J.; Baro, A. Angew. Chem. Int. Ed. 2003, 42, 1688.
13. Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
14. Krause, N.; Hoffmann-Roder, A. Synthesis 2001, 171.
15. Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033. For examples of asymmetric Michael additions of aldehydes and ketones to nitroolefins, see:
16. Pansare, S. V.; Pandya, K. J. Am. Chem. Soc. 2006, 128, 9624.
17. Reyes, E.; Vicario, J. L.; Badia, D.; Carrillo, L. Org. Lett. 2006, 8, 6135.
18. Xu, Y.; Cordova, A. Chem. Commun. 2006, 460.
19. Chi, Y.; Guo, L.; Kopf, N. A.; Gellman, S. H. J. Am. Chem. Soc. 2008, 130, 5608.
20. Enders, D.; Wang, C.; Bats, J. W. Angew. Chem. Int. Ed. 2008, 47, 7539.
21. Wiesner, M.; Revell, J. D.; Tonazzi, S.; Wennemers, H. J. Am. Chem. Soc. 2008, 130, 5610.
22. Lu, A.; Gao, P.; Wu, Y.; Wang, Y.; Zhou, Z.; Tang, C. Org. Biomol. Chem. 2009, 7, 3141.
23. Tan, B.; Zeng, X.; Lu, Y.; Chua, P. J.; Zhong, G. Org. Lett. 2009, 11, 1927.
24. Laars, M.; Ausmees, K.; Uudsemaa, M.; Tamm, T.; Kanger, T.; Lopp, M. J. Org. Chem. 2009, 74, 3772.
25. Wiesner, M.; Upert, G.; Angelici, G.; Wennemers, H. J. Am. Chem. Soc. 2010, 132, 6.
26. Zheng, Z.; Perkins, B. L.; Ni, B. J. Am. Chem. Soc. 2010, 132, 50.
27. Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84.
28. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F. III Synthesis 2004, 1509.
29. Notz, W.; Tanaka, F.; Barbas, C. F. III Acc. Chem. Res. 2004, 37, 580.
30. Huang, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170.
31. Yalalov, D. A.; Tsogoeva, S. B.; Schmatz, S. Adv. Synth. Catal. 2006, 348, 826.
32. Cao, C. L.; Ye, M. C.; Sun, X. L.; Tang, Y. Org. Lett. 2006, 8, 2901.
33. Jiang, X. X.; Zhang, Y. F.; Chan, A. S. C.; Wang, R. Org. Lett. 2009, 11, 153.
34. Wang, C.; Yu, C.; Liu, C. L.; Peng, Y. G. Tetrahedron Lett. 2009, 50, 2363.
35. Liu, J.; Yang, Z. G.; Liu, X. H.; Wang, Z.; Liu, Y. L.; Bai, S.; Lin, L. L.; Feng, X. M. Org. Biomol. Chem. 2009, 7, 4120.
36. Syu, S.-e.; Kao, T.-T.; Lin, W. Tetrahedron 2010, 66, 891.
37. Wang, J.; Li, H.; Lou, B.; Zu, L.; Guo, H.; Wang, W. Chem. Eur. J. 2006, 12, 4321.
38. Wojaczynska, E.; Wojaczynski, J. Chem. Rev. 2010, 110, 4303.
39. Fernandez, I.; Khiar, N. Chem. Rev. 2003, 103, 3651.
40. Bark, K.; Ellman, J. A. J. Am. Chem. Soc. 2009, 131, 3850.
41. Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010.
42. Singh, K. N.; Singh, P.; Singh, P.; Lal, N.; Sharma, S. K. Bioorg. Med. Chem. Lett. 2012, 22, 4225. Unpublished results from our laboratory.
43. Morris, D. J.; Partridge, A. S.; Manville, C. V.; Racys, D. T.; Woodward, G.; Docherty, G.; Wills, M. Tetrahedron Lett. 2010, 51, 209.
44. Hiskey, R. G.; Harpold, M. A. J. Org. Chem. 1967, 32, 3191.
45. Tsogoeva, S. B.; Wei, S. Chem. Commun. 2006, 451.
46. Wei, S.; Yalalov, D. A.; Tsogoeva, S. B.; Schmatz, S. Catal. Today 2007, 121, 151.
47. Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413.
48. Blarer, S. J.; Schweizer, B.; Seebach, D. Helv. Chim. Acta 1982, 65, 1637.
49. Blarer, S. J.; Seebach, D. Chem. Ber. 1983, 116, 3086.
50. In some asymmetric hydrogenations, high enantiomeric excess has been reported with the use of chiral ligands having a racemic chiral center at sulfur; see refs. 6b, 6d, and: Kvintovics, P.; James, B. R.; Heil, B. J. Chem. Soc., Chem. Commun. 1986, 1810.
51. Cobb, A. J. A.; Longbottom, D. A.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2004, 1808.
52. Cao, X.-Y.; Zheng, J.- C.; Li, Y.-X.; Shu, Z.-C.; Sun, X.-L.; Wang, B.-Q. Tetrahedron 2010, 66, 9703.
53. Mase, N.; Watanabe, K.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F. III J. Am. Chem. Soc. 2006, 128, 4996.
54. Vishnumaya , Singh, V. K. Org. Lett. 2007, 9, 1117.
55. Chen, J.-R.; Fu, L.; Zou, Y.-Q.; Chang, N.-J.; Rong, J.; Xiao, W.-J. Org. Biomol. Chem. 2011, 9, 5280.
56. Sun, Z.-W.; Peng, F.-Z.; Li, Z.-Q.; Zou, L.-W.; Zhang, S.-X.; Li, X.; Shao, Z.-H. J. Org. Chem. 2012, 77, 4103.
57. Chuan, Y.-M.; Yin, L.-Y.; Zhang, Y.-M.; Peng, Y.-G. Eur. J. Org. Chem. 2011, 578.
58. Furniss, B. S. Vogels Textbook of Practical Organic Chemistry, 4th ed.; ELBS/Longman: London, 1978, 796.
59. The preparation of racemic 5 and 6 has been reported, see: Quinet, C.; Sampoux, L.; Marko, I. E. Eur. J. Org. Chem. 2009, 1806.
60. Lu, A.; Wu, R.; Wang, Y.; Zhou, Z.; Wu, G.; Fang, J.; Tang, C. Eur. J. Org. Chem. 2011, 122.
61. Karthikeyan, T.; Sankararaman, S. Tetrahedron: Asymmetry 2008, 19, 2741.
62. Xu, D.-Q.; Wang, B.-T.; Luo, S.-P.; Yue, H. D.; Wang, L.-P.; Xu, Z.-Y. Tetrahedron: Asymmetry 2007, 18, 1788.
63. Xu, D.-Z.; Shi, S.; Wang, Y. Eur. J. Org. Chem. 2009, 4848.
64. Gang, C.; Zheng, W.; Kuiling, D. Chin. J. Chem. 2009, 27, 163.
65. Chunhua, L.; Da-Ming, D. Synthesis 2011, 1968.
66. Mandal, T.; Zhao, C.-G. Angew. Chem. Int. Ed. 2008, 47, 7714.
67. Yu, C.; Qiu, J.; Zheng, F.; Zhong, W. Tetrahedron Lett. 2011, 52, 3298.
68. McCooey, S. H.; Connon, S. J. Org. Lett. 2007, 9, 599.
69. Xue, F.; Zhang, S.; Duan, W.; Wang, W. Adv. Synth. Catal. 2008, 350, 2194.
70. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112.
71. CCDC 928286 contains the supplementary crystallographic data for 6. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif.