Formal highly enantioselective organocatalytic addition of alkyl anions to α,β-unsaturated aldehydes: Application to the synthesis of isotope-enantiomers

Chemistry - A European Journal

Volumn 15, Issue 42, 2009, Pages 11095-11099

  Alba, Andrea Nekane ^a   Companyó, Xavier ^a   Moyano, Albert ^a   Rios, Ramon ^a,b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b ICC Researcher at UB ^*

Author keywords

Enantioselective addition; Isotope effects; Organocatalysis; Sulfones; Unsaturated aldehydes

Indexed keywords

ENANTIOSELECTIVE ADDITION; ISOTOPE EFFECTS; ORGANOCATALYSIS; SULFONES; UNSATURATED ALDEHYDES;

AMINES; CARRIER MOBILITY; CATALYSIS; CHROMATOGRAPHIC ANALYSIS; COLUMN CHROMATOGRAPHY; ISOTOPES; METHANE; ORGANOMETALLICS; RATE CONSTANTS; REACTION KINETICS; TOLUENE;

ALDEHYDES;

EID: 70350512581     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901806     Document Type: Article

References (63)

1. a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
2. b) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
3. c) Catalytic Asymmetric Synthesis, 2nd éd. (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000;
4. d) Transition Metals for Organic Synthesis, 2nd ed. (Eds.: M. Beller, C. BoIm), Wiley-VCH, Weinheim, 2004.
5. For authoritative reviews on the topic of organocatalysis: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840;
6. Angew. Chem. Int. Ed. 2001, 40, 3726;
7. b) B. List, Synlett 2001, 1675;
8. c) B. List, Tetrahedron 2002, 58, 2481;
9. d) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 226, 5248;
10. Angew. Chem. Int. Ed. 2004, 43, 5138;
11. e) A. Berkessel, H. Groger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005;
12. f) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719;
13. g) G. Leiais, D.W.C. MacMillan, Aldrichimica Acta 2006, 39, 79;
14. h) D. Almasi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007,18, 299-365.
15. B. List, R. A Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396.
16. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244.
17. S. R. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minnaard, B. L. Feringa, Chem. Rev. 2008, 108, 2824-2852.
18. A. Alexakis, J. E. Bäckvall, N. Krause, O. Pamies, M. Dieguez, Chem. Rev. 2008,108, 2796-2823.
19. S. Ay, M. Nieger, S. Bräse, Chem. Eur. J. 2008,14, 11539-11556.
20. S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jorgensen, Angew. Chem. 2006, 118, 4411-4415;
21. Angew. Chem. Int. Ed. 2006, 45,4305-4309.
22. For recent application of malonate addition for the synthesis of pyrrolidines: a) R. Rios, J. Vesely, I. Ibrahem, H. Sunden, A. Cordova, Tetrahedron Lett. 2007, 48, 8695-8699; for the synthesis of piperidines:
23. b) G. Valero, J. Schimer, I. Cisarova, J. Vesely, A. Moyano, R. Rios, Tetrahedron Lett. 2009, 50,1943-1946; for the synthesis of quinolizilidine derivatives:
24. c) J. Franzén, A. Fisher, Angew. Chem. 2009, 121, 1377-1377;
25. Angew. Chem. Int. Ed. 2009, 48, 1351-1354.
26. a) S. Cabrera, J. Aleman, P. Bolze, S. Bertelsen, K. A. Jorgensen, Angew. Chem. 2008, 120, 127-131;
27. Angew. Chem. Int. Ed. 2008, 47, 121-125;
28. b) A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jorgensen, Chem. Commun. 2006, 4928-4930.
29. a) Y. Wang, P. Li, X. Liang, T. Zhang, J. Ye, Chem. Commun. 2008, 1232-1234;
30. b) L. Zu, H. Xie, H. Li, J. Wang, W. Wang, Adv. Synth. Catal. 2007, 349,2660-2664.
31. N-Nucleophiles: a) I. Ibrahem, R. Rios, J. Vesely, G.-L. Zhao, A. Cordova, Chem. Commun. 2007, 849-852;
32. b) Y. K. Chen, Y. Masanori, D.W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328-9329.
33. O-Nucleophiles: a) H. Sunden, I. Ibrahem, G.-L. Zhao, L. Erikson, A. Cordova, Chem. Eur. J. 2007, 13, 574-581;
34. b) H. Li, J. Wang, T. E-Nunu, L. Zu, W. Jiang, W. Wang, Chem. Commun. 2007, 507-509. S-Nucleophiles:
35. c) M. Marigo, T. Schulte, J. Franzen, K. A. Jorgensen, J. Am. Chem. Soc. 2005, 127, 15710-15711;
36. d) R. Rios, H. Sunden, I. Ibrahem, G.-L. Zhao, L. Erikson, A. Cordova, Tetrahedron Lett. 2006, 47, 8679-8682;
37. e) W. Wang, H. Hao, J. Wang, L. Zu, J. Am. Chem. Soc. 2006,128, 10354-10355.
38. B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. 1997,109, 1562-1564;
39. Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489.
40. a) G. K. S. Prakash, X. Zhao, S. Chacko, F. Wang, H. Vaghoo, G. A. Olah, Beilstein J. Org. Chem. 2008, 4, 17;
41. b) G. K. S. Prakash, S. Chacko, S. Alconcel, T. Stewart, T. Mathew, G. A. Olah, Angew. Chem. 2007,119, 5021-5024;
42. Angew. Chem. Int. Ed. 2007, 46, 4933- 4936;
43. c)T. Fukuzumi, N. Shibata, M. Sugiura, H. Yasui, S. Nakamura, T. Toru, Angew. Chem. 2006, 118, 5095-5099;
44. Angew. Chem. Int. Ed. 2006, 45, 4973-4977;
45. d) S. Mizuta, N. Shibata, Y. Goto, T. Furukawa, S. Nakamura, T. Toru, J. Am. Chem. Soc. 2007, 129, 6394-6395;
46. e) T. Furukawa, N. Shibata, S. Mizuta, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008,120, 8171-8174;
47. Angew. Chem. Int. Ed. 2008, 47, 8051 -8054;
48. f) during the preparation of this manuscript, Prakash et al. described a stereoselective 1,4-addition of afluoro-a-nitro(phenylsulfonyl)methane to chalcones, using cinchonabased bifunctional catalysts: G. K. S. Prakash, F. Wang, T. Stewart, T. Matthew, G. A. Olah, Proc. Natl. Acad. Sci. USA 2009, 106, 4090-4094.
49. A.-N. Alba, X. Companyó, A. Moyano, R. Rios, Chem. Eur. J. 2009, 25,7035-7038.
50. a) A.-N. Alba, N. Bravo, A. Moyano, R. Rios, Tetrahedron Lett. 2009, 50, 3067-3069;
51. b)J. Veselý, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Chem. Eur. J. 2008, 14, 2693-2698;
52. c) R. Rios, H. Sunden, I. Ibrahem, G.-L Zhao, A. Córdova, Tetrahedron Lett. 2006, 47, 8679-8682;
53. d) R. Rios, H. Sunden, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2007, 48, 2181-2184;
54. e) R. Rios, I. Ibrahem, J. Vesely, G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2007, 48, 5701-5705;
55. f) R. Rios, J. Vesely, H. Sundén, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2007, 48, 5835-5839.
56. K. Tanaka, D. J. Aberhardt, J. L. Amster, E. E. Jenkins, C.-T. Hau, J. Biol. Chem. 1980,255, 7763-7768.
57. J. C. Shattuck, J. Meinwald, Tetrahedron Lett. 1997, 38, 8461-8464.
58. a) T. Kawasaki, Y Matsumura, T. Tsutsumi, K. Suzuki, M. Ito, K. Soai, Science 2009, 324, 492-495;
59. b) T. Shibata, K. Iwahashi, T. Kawasaki, K. Soai, Tetrahedron: Asymmetry 2007,18, 1759-1762.
60. B. List, J. Am. Chem. Soc. 2002,124, 5656-5657.
61. A. Bogevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jorgensen, Angew. Chem. 2002,114, 1868-1871;
62. Angew. Chem. Int. Ed. 2002,42,1790-1793.
63. D. J. Aberhart, B. H. Weiller, J. Labelled Comd. Radiopharm. 1982, 20, 663-668.