Proline catalyzed two-component, three-component and self-asymmetric Mannich reactions promoted by ultrasonic conditions

Tetrahedron Letters

Volumn 47, Issue 33, 2006, Pages 5965-5967

  Kantam, M Lakshmi ^a   Rajasekhar, Ch V ^a   Gopikrishna, G ^a   Rajender Reddy, K ^a   Choudary, B M ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b Ogene Systems I Pvt Ltd   (India)

Author keywords

Asymmetric synthesis; Mannich reaction; Organo catalysis; Proline; Ultrasonic conditions

Indexed keywords

ACETONE; GLYCOLIC ACID; PROLINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; MANNICH REACTION; STEREOCHEMISTRY; ULTRASOUND;

EID: 33745712182     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.042     Document Type: Article

References (39)

1. For reviews, see. In: Trost B.M., Fleming I., and Kleinmann E.F. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon Press, New York Chapter 4.1
2. Arend M., Westermann B., and Risch N. Angew. Chem., Int. Ed. 37 (1998) 1044-1070
3. Cordova A. Acc. Chem. Res. 37 (2004) 102-112
4. In: Berkessel A., and Groger H. (Eds). Asymmetric Organocatalysis (2005), Wiley-VCH, Weinheim
5. Kobayashi S., and Ueno M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Supplement 1 (2003), Springer, Berlin Chapter 29.5
6. Trost B.M., and Terrell L.R. J. Am. Chem. Soc. 125 (2003) 338-339
7. Olleyier T., and Nadeau E. J. Org. Chem. 69 (2004) 9292-9295
8. Matsunaga S., Yoshida T., Morimoto H., Kumagai N., and Shibasaki M. J. Am. Chem. Soc. 126 (2004) 8777-8785
9. Hamashima Y., Sasamoto N., Hotta D., Somei H., Umebayashi N., and Sodeoka M. Angew. Chem., Int. Ed. 44 (2005) 1525-1529
10. List B., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 122 (2000) 2395-2396
11. Sakthivel K., Notz W., Bui T., and Barbas III C.F. J. Am. Chem. Soc. 123 (2001) 5260-5267
12. For reviews, see:. List B. Tetrahedron 58 (2002) 5573-5590
13. List B. Synlett (2001) 1675-1686
14. List B. Acc. Chem. Res. 37 (2004) 548-557
15. Notz W., Tanaka F., and Barbas III C.F. Acc. Chem. Res. 37 (2004) 580-591
16. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
17. List B. J. Am. Chem. Soc. 122 (2000) 9336-9337
18. List B., Pojarliev P., Biller W.T., and Martin H.J. J. Am. Chem. Soc. 124 (2002) 827-833
19. Notz W., Sakthivel K., Bui T., Zhong G., and Barbas III C.F. Tetrahedron Lett. 42 (2001) 199-201
20. Juhl K., Gathergood N., and Jorgensen K.A. Angew. Chem., Int. Ed. 40 (2001) 2995-2997
21. Zhuang W., Saaby S., and Jørgensen K.A. Angew. Chem., Int. Ed. 43 (2004) 4476-4478
22. Munch A., Wendt B., and Christmann M. Synlett (2004) 2751-2755
23. Ibrahem I., Casas J., and Cordova A. Angew. Chem., Int. Ed. 43 (2004) 6528-6531
24. Cobb A.J.A., Shaw D.M., Longbottom D.A., Gold J.B., and Ley S.V. Org. Biomol. Chem. 3 (2005) 84-96
25. Cordova A., Notz W., Zhong G., Betancort J.M., and Barbas III C.F. J. Am. Chem. Soc. 124 (2002) 1842-1843
26. Cordova A., Watanabe S.-I., Tanaka F., Notz W., and Barbas III C.F. J. Am. Chem. Soc. 124 (2002) 1866-1867
27. Hayashi Y., Tsuboi W., Shoji M., and Suzuki N. J. Am. Chem. Soc. 125 (2003) 11208-11209
28. Ibrahem I., and Cordova A. Tetrahedron Lett. 46 (2005) 3363-3367
29. Westermann B., and Neuhaus C. Angew. Chem., Int. Ed. 44 (2005) 4077-4079
30. Enders D., Grondal C., Vrettou M., and Raabe G. Angew. Chem., Int. Ed. 44 (2005) 4079-4083
31. Zhao D., Wu M., Kou Y., and Min E. Catal. Today 74 (2002) 157-189
32. Cravotto G., and Cinta P. Chem. Soc. Rev. 35 (2006) 180-196
33. de la Hoz A., Diaz-Ortiz A., and Moreno A. Chem. Soc. Rev. 34 (2005) 164-178
34. Sreedhar B., Surendra Reddy P., Prakash B.V., and Ravindra A. Tetrahedron Lett. 41 (2005) 7019-7022
35. Chowdari N.S., Ramachary D.B., and Barbas III C.F. Synlett (2003) 1906-1909
36. Rodriguez B., and Bolm C. J. Org. Chem. 71 (2006) 2888-2891
37. Cordova A. Synlett (2003) 1651-1654
38. Cordova A. Chem. Eur. J. 10 (2004) 1987-1997
39. Hayashi Y., Tsuboi W., Ashimine I., Urushima T., Shoji M., and Sakai K. Angew. Chem., Int. Ed. 42 (2003) 3677-3680