Enantioselective double aldol reaction catalyzed by chiral phosphine oxide

Chemistry - A European Journal

Volumn 17, Issue 29, 2011, Pages 7992-7995

  Shimoda, Yasushi ^a   Kotani, Shunsuke ^a   Sugiura, Masaharu ^a   Nakajima, Makoto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

aldol reaction; asymmetric catalysis; domino reactions; intramolecular enolization; Lewis base

Indexed keywords

ALDOL REACTIONS; ASYMMETRIC CATALYSIS; DOMINO REACTIONS; ENOLIZATION; LEWIS BASE;

CATALYSIS; PHOSPHORUS COMPOUNDS; REACTION KINETICS;

CONDENSATION REACTIONS;

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; OXIDE; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; CATALYSIS; OXIDES; PHOSPHINES; STEREOISOMERISM;

EID: 79959962212     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100917     Document Type: Article

References (46)

1. For reviews of sequential reactions, see: a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170
2. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163
3. L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
4. For borane-mediated double aldol reactions, see: a) A. Abiko, J.-F. Liu, D. C. Buske, S. Moriyama, S. Masamune, J. Am. Chem. Soc. 1999, 121, 7168-7169
5. A. Abiko, T. Inoue, S. Masamune, J. Am. Chem. Soc. 2002, 124, 10759-10764
6. H. Furuno, T. Inoue, A. Abiko, Tetrahedron Lett. 2002, 43, 8297-8299
7. A. Abiko, Acc. Chem. Res. 2004, 37, 387-395.
8. For a triple aldol cascade reaction, see:, B. J. Albert, H. Yamamoto, Angew. Chem. 2010, 122, 2807-2809
9. Angew. Chem. Int. Ed. 2010, 49, 2747-2749.
10. For stepwise double aldol reactions, see: a) T. Mukaiyama, H. Arai, I. Shiina, Chem. Lett. 2000, 580-581
11. H. Arai, I. Shiina, T. Mukaiyama, Chem. Lett. 2001, 118-119
12. T. Mukaiyama, K. Pubhom, K. Yamane, H. Arai, Bull. Chem. Soc. Jpn. 2003, 76, 413-425.
13. For reviews on direct aldol reactions, see: a)B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601
14. M. Shibasaki, N. Yoshkawa, Chem. Rev. 2002, 102, 2187-2209
15. S. Saito, H. Yamamoto, Acc. Chem. Res. 2004, 37, 570-579
16. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580-591
17. G. Guillena, C. Nájera, D. J. Róamn, Tetrahedron: Asymmetry 2007, 18, 2249-2293
18. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
19. For leading and recent papers on direct asymmetric aldol reactions, see: a)Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944
20. Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873
21. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396
22. B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003-12004
23. T. Suzuki, N. Yamagiwa, Y. Matsuo, S. Sakamoto, K. Yamaguchi, M. Shibasaki, R. Noyori, Tetrahedron Lett. 2001, 42, 4669-4671
24. S. S. V. Ramasastry, K. Albertshofer, N. Utsumi, C. F. Barbas III, Org. Lett. 2008, 10, 1621-1624
25. Y. Hayashi, T. Itoh, S. Aratake, H. Ishikawa, Angew. Chem. 2008, 120, 2112-2114
26. Angew. Chem. Int. Ed. 2008, 47, 2082-2084
27. K. Nakayama, K. Maruoka, J. Am. Chem. Soc. 2008, 130, 17666-17667
28. K. Baer, M. KrauAßer, E. Burda, W. Hummel, A. Berkessel, H. Gröger, Angew. Chem. 2009, 121, 9519-9522
29. Angew. Chem. Int. Ed. 2009, 48, 9355-9358
30. M. Iwata, R. Yazaki, Y. Suzuki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 18244-18245
31. H. Ube, N. Shimada, M. Terada, Angew. Chem. 2010, 122, 1902-1905
32. Angew. Chem. Int. Ed. 2010, 49, 1858-1861.
33. S. Kotani, Y. Shimoda, M. Sugiura, M. Nakajima, Tetrahedron Lett. 2009, 50, 4602-4605
34. S. Kotani, S. Aoki, M. Sugiura, M. Nakajima, Tetrahedron Lett. 2011, 52, 2834-2836.
35. S. Kotani, S. Hashimoto, M. Nakajima, Synlett 2006, 1116-1118
36. S. Kotani, S. Hashimoto, M. Nakajima, Tetrahedron 2007, 63, 3122-3132; for related chiral phosphine oxide-catalyzed reductive aldol reactions, see
37. M. Sugiura, N. Sato, S. Kotani, M. Nakajima, Chem. Commun. 2008, 4309-4311
38. M. Sugiura, N. Sato, Y. Sonoda, S. Kotani, M. Nakajima, Chem. Asian J. 2010, 5, 478-481.
39. For reviews on Lewis base organocatalysts, see: a) Y. Orito, M. Nakajima, Synthesis 2006, 1391-1401
40. A. V. Malkov, P. Kočovský, Eur. J. Org. Chem. 2007, 29-36
41. S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584-1663
42. Angew. Chem. Int. Ed. 2008, 47, 1560-1638
43. M. Benaglia, S. Rossi, Org. Biomol. Chem. 2010, 8, 3824-3830.
44. (R)-BQNO was prepared according to the literature, see:, M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419-6420.
45. Small amounts (<5%) of mono-aldol adduct were obtained in most cases.
46. (R)-and (S)-4a were prepared following the procedure, see:, M. Nakajima, Y. Orito, T. Ishizuka, S. Hashimoto, Org. Lett. 2004, 6, 3763-3765.