Amine-catalyzed direct self Diels-Alder reactions of α,β-unsaturated ketones in water: Synthesis of pro-chiral cyclohexanones

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6743-6746

  Ramachary, D B ^a   Chowdari, Naidu S ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Amines; Aqueous media; Cyclohexanones; Diels Alder reactions; Enamines; Imines; Organocatalysis

Indexed keywords

1,3 BUTADIENE DERIVATIVE; AMINE; CYCLOHEXANONE DERIVATIVE; KETONE DERIVATIVE; PROLINE; PYRROLIDINE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; ROOM TEMPERATURE; STEREOCHEMISTRY;

BETULACEAE;

EID: 0037119742     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01500-9     Document Type: Article

References (27)

1. Reviews: (a) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. III, p. 1177;
2. (b) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
3. Northrup A.B., MacMillan D.W.C. J. Am. Chem. Soc. 124:2002;2458.
4. List B., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 122:2000;2395.
5. Sakthivel K., Notz W., Bui T., Barbas C.F. III. J. Am. Chem. Soc. 123:2001;5260.
6. Saito S., Nakadai M., Yamamoto H. Synlett. 2001;1245.
7. Betancort J.M., Sakthivel K., Thayumanavan R., Barbas C.F. III. Tetrahedron Lett. 42:2001;4441.
8. Betancort J.M., Barbas C.F. III. Org. Lett. 3:2001;3737.
9. Notz W., Sakthivel K., Bui T., Barbas C.F. III. Tetrahedron Lett. 42:2001;199.
10. Cordova A., Notz W., Zhong G., Betancort J.M., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1842.
11. Cordova A., Watanabe S., Tanaka F., Notz W., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1866.
12. Hajos Z.G., Parrish D.R. J. Org. Chem. 39:1974;1615.
13. Eder U., Sauer G., Wiechert R. Angew. Chem., Int. Ed. Engl. 10:1971;496.
14. Bui T., Barbas C.F. III. Tetrahedron Lett. 41:2000;6951.
15. Thayumanavan R., Dhevalapally B., Sakthivel K., Tanaka F., Barbas C.F. III. Tetrahedron Lett. 43:2002;3817.
16. For double Michael reactions of α,β-unsaturated ketones, see: (a) Hallnemo, G.; Ullenius, C. Tetrahedron 1983, 39, 1621;
17. (b) Ueda, T.; Otsuji, Y. Chem. Lett. 1986, 1635;
18. (c) Mukaiyama, T.; Sagawa, Y.; Kobayashi, S. Chem. Lett. 1986, 1821;
19. (d) Oren, J.; Demuth, M.; Fuchs, B. Synthesis 1987, 850;
20. (e) Kanemasa, S.; Kumegawa, M.; Wada, E.; Nomura, M. Bull. Chem. Soc. Jpn. 1991, 64, 2990;
21. (f) Takeuchi, N.; Handa, S.; Koyama, K.; Kamata, K.; Goto, K.; Tobinaga, S. Chem. Pharm. Bull. 1991, 39, 1655;
22. (g) Gossnitzer, E.; Wendelin, W.; Schermanz, K.; Frieberger, K. Monatsh. Chem. 2001, 132, 1081;
23. (h) Asato, A. E.; Watanabe, C.; Li, Xiao-Yuan.; Liu, R. S. H.; Tetrahedron Lett. 1992, 33, 3105.
24. + calcd 327.0484, found 327.0487.
25. The moderate yield originated primarily due to product losses that result from their low solubility. Reaction conversion was very good.
26. Breslow R. Acc. Chem. Res. 24:1991;159.
27. Enantiomeric excess was determined by chiral-phase HPLC analyses. Absolute stereochemistry was not determined.