Domino hydroformylation/enantioselective cross-aldol addition

Advanced Synthesis and Catalysis

Volumn 349, Issue 11-12, 2007, Pages 1891-1895

  Abillard, Olivier ^a   Breit, Bernhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Aldol reaction; Asymmetric synthesis; Domino reactions; Homogeneous catalysis; Hydroformylation; Organocatalysis

Indexed keywords

EID: 34548514454     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700216     Document Type: Article

References (50)

1. a) B. M. Trost, Angew. Chem. 1995, 107, 285-307;
2. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281;
3. b) B. M. Trost, Science 1991, 254, 1471-1477.
4. a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944;
5. Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873;
6. b) N. Yoshikawa, Y. M. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168-4178;
7. c) N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Oshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466-2467;
8. d) N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2169-2178.
9. a) B. M. Trost, H. Ito , J. Am. Chem. Soc. 2000, 122, 12003-12004;
10. b) B. M. Trost, E. R. Silcoff, H. Ito, Org. Lett. 2001, 3, 2497-2500;
11. c) B. M. Trost, L. R. Terell, J. Am. Chem. Soc. 2003, 125, 338-339;
12. d) B. M. Trost, A. Fettes, B. T. Shireman, J. Am. Chem. Soc. 2004, 126, 2660-2661;
13. e) B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778-2779.
14. R. Mahrwald, B. Costisella, B. Gündogan, Synthesis 1997, 262-264;
15. R. Mahrwald, B. Schetter, Org. Lett. 2006, 8, 281-284.
16. a) B. List, W. Notz, J. Am. Chem. Soc. 2000, 122, 7386-7387;
17. b) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575;
18. c) B. List, R. Lerner, C. F. Barbas III. , J. Am. Chem. Soc. 2000, 122, 2395-2396.
19. a) S. Kandasamy, W. Notz, T. Bui, C. F. Barbas III. , J. Am. Chem. Soc. 2001, 123, 5260-5267;
20. b) A. Cordova, W. Notz, C. F. Barbas III. , J. Org. Chem. 2002, 67, 301-303.
21. a) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798-6799;
22. b) R. I. Storer, D. W. C. MacMillan, Tetrahedron 2004, 60, 7705-7714;
23. c) I. K. Mangion, A. B. Northrup, D. W. C. MacMillan, Angew. Chem. 2004, 116, 6890-6892;
24. Angew. Chem. Int. Ed. 2004, 43,6722-6724.
25. a) A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204-2206;
26. Angew. Chem. Int. Ed. 2004, 43, 2152-2154;
27. b) D. Enders, C. Grondal, Angew. Chem. 2005, 117, 1235-1238;
28. Angew. Chem. Int. Ed. 2005, 44, 1210-1212.
29. For an intramolecular variant see: C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003, 115, 2891-2894;
30. Angew. Chem. Int. Ed. 2003, 42, 2785-2788.
31. For reviews on hydroformylation see: B. Breit, in: Science of Synthesis, Vol. 25. (Ed. : R. Brückner), Georg Thieme Verlag, Stuttgart, New York, 2007, pp 277-318;
32. Rhodium Catalyzed Hydroformylation, (Eds.: P. W. N. M. van Leeuwen, C. Claver), Kluwer: Dordrecht, The Netherlands, 2000;
33. B. Breit, Acc.Chem. Res. 2003, 36, 264-275.
34. For the concept of domino reactions in organic synthesis, see a) L. F. Tietze, A. Modi, Med. Res. Rev. 2000, 20, 304-322;
35. b) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
36. c) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170;
37. Angew. Chem. Int. Ed. 1993, 32, 131-163;
38. d) T. L. Ho, Tandem Organic Reactions, Wiley, New York 1992.
39. For the use the hydroformylation as part of sequential reactions see: a) P. Eilbracht, L. Bärfacker, C. Buss, C. Hollmann, B. E. Kitsos-Rzychon, C. L. Kranemann, T. Rische, R. Roggenbuck, A. Schmidt, Chem. Rev. 1999, 99, 3329-3365;
40. b) B. Breit, S. K. Zahn, Angew. Chem. 1999, 111, 1022-1024;
41. Angew. Chem. Int. Ed. 1999, 38, 969-971;
42. c) B. Breit, S. K. Zahn, Angew. Chem. 2001, 113, 1964-1967;
43. Angew. Chem. Int. Ed. 2001, 40, 1910-1913;
44. d) M. D. Keränen, P. Eilbracht, Org. Biomol. Chem. 2004, 2, 1688-1690.
45. a) B. Breit, W. Seiche, J. Am. Chem. Soc. 2003, 125, 6608-6609;
46. b) W. Seiche, A. Schuschkowski, B. Breit, Adv. Synth. Cat. 2005, 1488-1494.
47. [7a]
48. A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84-96.
49. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804-807;
50. Angew. Chem. Int. Ed. 2005, 44, 794-797.