Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes

Organic Letters

Volumn 3, Issue 4, 2001, Pages 573-575

  List, Benjamin ^a   Pojarliev, Peter ^a   Castello, Chris ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; IPSENOL; KETONE; PROLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; ALDEHYDES; CATALYSIS; KETONES; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 0035932079     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006976y     Document Type: Article

References (26)

1. List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. Proline-catalyzed intramolecular enantiogroup-differentiating aldol reactions have been pioneered by: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621.
2. List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. Proline-catalyzed intramolecular enantiogroup-differentiating aldol reactions have been pioneered by: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621.
3. List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. Proline-catalyzed intramolecular enantiogroup-differentiating aldol reactions have been pioneered by: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621.
4. Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386-7387.
5. Unpublished result.
6. For an excellent review, see: Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389.
7. For reviews, see: (a) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473.
8. (b) Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352-1374.
9. Turner, J. M.; Bui, T.; Lerner, R. A.; Barbas, C. F., III; List, B. Chem.-Eur. J. 2000, 2772-2774.
10. List, B.; Shabat, D.; Barbas, C. F., III.; Lerner, R. A. Chem. Eur. J. 2000, 881-885.
11. (b) Shabat, D.; List, B.; Lerner, R. A.; Barbas, C. F., III. Tetrahedron. Lett. 1999, 40, 1437-1440.
12. Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178.
13. Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873. Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178.
14. (b) Trost, B. M.; Hisanaka, I. J. Am. Chem. Soc. 2000, 122, 12003-12004.
15. Silverman, I. R.; Edington, C.; Elliott, J. D.; Johnson, W. S J. Org. Chem. 1987, 52, 180-183.
16. 3, > 25% yield. Acetone and chloroform are also useful solvents in proline-catalyzed Mannich reactions: List, B. J. Am. Chem. Soc. 2000, 122, 9336-9337.
17. Unpublished results. The four stereoisomeric products of the proline-catalyzed aldol reaction between cyclohexanone and benzaldehdye are known and have been characterized by: Denmark, S. E.; Stavenger, R. A.; Wong, K.-T; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991.
18. 3 with L-proline for 3 days did not yield any significant amounts of enone 5e.
19. Oertle, K.; Beyeler, H.; Duthaler, R. O.; Lottenbach, W.; Riediker, M.; Steiner, E. Helv. Chim. Acta 1990, 72, 353-358.
20. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
21. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033-3040.
22. For selected asymmetric syntheses of ipsenol, see: (a) Mori, K. Tetrahedron Lett. 1975, 26, 2187-2190.
23. (b) Ikeda, N.; Arai, I.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 483-486.
24. (c) Brown, H. C.; Randad, R. S. Tetrahedron Lett. 1990, 31, 455-458.
25. (d) Trost, B. M.; Rodriguez, M. S. Tetrahedron Lett. 1992, 33, 4675-4678. Also see ref 13.
26. S = 15.7 min). Almost identical results were obtained using an aqueous workup (phosphate-buffered saline/ethyl acetate). All new compounds described herein gave satisfactory spectroscopic data.