Catalytic microwave-promoted direct aldol condensation using resin-bound secondary amine

Synthetic Communications

Volumn 44, Issue 2, 2014, Pages 161-169

  Liao, Fu Xu ^a   Wang, Yu Guang ^a   Zhu, Qing ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Aldol reaction; imino group; microwave; polymer supported reagents; recyclability

Indexed keywords

AMINE; POLYSTYRENE; RESIN;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; MICROWAVE RADIATION;

EID: 84887481952     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.793775     Document Type: Article

References (34)

1. Alcaide, B.;, Almendros, P. The direct catalytic asymmetric aldol reaction. Eur. J. Org. Chem. 2002, 1595-1601.
2. Saito, S.;, Yamamoto, H. Design of acid-base catalysis for the asymmetric direct Aldol reaction. Acc. Chem. Res. 2004, 37, 570-579.
3. Palomo, C.;, Oiarbide, M.;, Garcá, J. M. Current progress in the asymmetric aldol addition reaction. Chem. Soc. Rev. 2004, 33, 65-75.
4. Dalko, P. I.;, Moisan, L. In the golden age of organocatalysis. Angew. Chem. Int. Ed. 2004, 43, 5138-5175.
5. Keck, G. E.;, Wager, C. A.;, Sell, T.;, Wager, T. T. An especially convenient stereoselective reduction of β -hydroxy ketones to anti-1,3-diols using samarium diiodide. J. Org. Chem. 1999, 64, 2172-2173.
6. Sakthivel, K.;, Notz, W.;, Bui, T.;, Barbas C. F. III. Amino acid-catalyzed direct asymmetric aldol reactions: A bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions. J. Am. Chem. Soc. 2001, 123, 5260-5267.
7. Córdova, A.;, Notz, W.;, Zhong, G.;, Betancort, J. M.;, Barbas III, C. F. A highly enantioselective amino acid-catalyzed route to functionalized -amino acids. J. Am. Chem. Soc. 2002, 124, 1842-1843.
8. Michelangelo, G.;, Francesco, G.;, Renato, N. Supported proline and proline-derivatives as recyclable organocatalysts. Chem. Soc. Rev. 2008, 37, 1666-1688.
9. Giacalone, F.;, Gruttadauria, M.;, Marculescu, A. M.;, Anna, F. D.;, Noto, R. Polystyrene-supported proline as recyclable catalyst in the Baylis-Hillman reaction of arylaldehydes and methyl or ethyl vinyl ketone. Catal. Commun. 2008, 9, 1477-1481.
10. Utsumi, N.;, Zhang, H.;, Tanaka, F.;, Barbas III, C. F. A way to highly enantiomerically enriched aza-Morita-Baylis-Hillman-type products. Angew. Chem. Int. Ed. 2007, 46, 1878-1880.
11. List, B. Proline-catalyzed asymmetric reactions. Tetrahedron 2002, 58, 5573-5590.
12. Jarvo, E. R.;, Miller, S. J. Amino acids and peptides as asymmetric organocatalysts. Tetrahedron. 2002, 58, 2481-2495.
13. List, B.;, Lerner, R. A.;, Barbas III, C. F. Proline-catalyzed direct asymmetric aldol reactions. J. Am. Chem. Soc. 2000, 122, 2395-2396.
14. Kim, H.;, MacMillan, D. W. C. Enantioselective organo-SOMO catalysis: The -vinylation of aldehydes. J. Am. Chem. Soc. 2008, 130, 398-399.
15. Hayashi, Y.;, Gotoh, H.;, Hayashi, T.;, Shoji, M. Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes. Angew. Chem. Int. Ed. 2005, 44, 4212-4215.
16. Kano, T.;, Takai, J.;, Tokuda, O.;, Maruoka, K. Design of an axially chiral amino acid with a binaphthyl backbone as an organocatalyst for a direct asymmetric aldol reaction. Angew. Chem. Int. Ed. 2005, 44, 3055-3057.
17. Xiao, J.;, Lu, Y. P.;, Liu, Y. L.;, Wong, P. S.;, Loh, T. P. A new class of structurally rigid tricyclic chiral secondary amine organocatalyst: Highly enantioselective organocatalytic Michael addition of aldehydes to vinyl sulfones. Org. Lett. 2011, 13, 876-879.
18. Gruttadauria, M.;, Giacalone, F.;, Marculescu, A. M.;, Meo, P. L.;, Riela, S.;, Noto, R. Hydrophobically directed aldol reactions: Polystyrene-supported L-proline as a recyclable catalyst for direct asymmetric aldol reactions in the presence of water. Eur. J. Org. Chem. 2007, 4688-4698.
19. Mase, N.;, Tanaka, F.;, Barbas III, C. F. Rapid fluorescent screening for bifunctional amine-acid catalysts: Efficient syntheses of quaternary carbon-containing aldols under organocatalysis. Org. Lett. 2003, 5, 4369-4372.
20. Nakadai, M.;, Saito, S.;, Yamamoto, H. Diversity-based strategy for discovery of environmentally benign organocatalyst: Diamine-protonic acid catalysts for asymmetric direct aldol reaction. Tetrahedron 2002, 58, 8167-8177.
21. Tang, Z.;, Jiang, F.;, Yu, L.;, Cui, X.;, Gong, L.;, Mi, A.;, Jiang, Y.; Wu. Y. Novel small organic molecules for a highly enantioselective direct aldol reaction. J. Am. Chem. Soc. 2003, 125, 5262-5263.
22. Bahmanyar, S.;, Houk, K. N.;, Martin, H. J.;, List, B. Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions. J. Am. Chem. Soc. 2003, 125, 2475-2479.
23. Cozzi, F. Immobilization of organic catalysts: When, why, and how. Adv. Synth. Catal. 2006, 348, 1367-1390.
24. Benaglia, M.;, Puglisi, A.;, Cozzi, F. Polymer-supported organic catalysts. Chem. Rev. 2003, 103, 3401-3429.
25. Fraile, J. M.;, Garcia, J. I.;, Mayoral, J. A. Noncovalent immobilization of enantioselective catalysts. Chem. Rev. 2009, 109, 360-417.
26. Chen, J. R.;, Lu, H. H.;, Li, X. Y.;, Cheng, L.;, Wan, J.;, Xiao, W. J. Readily tunable and bifunctional L-prolinamide derivatives: Design and application in the direct enantioselective aldol reactions. Org. Lett. 2005, 7, 4543-4545.
27. Font, D.;, Jimeno, C.;, Pericás, M. A. Polystyrene-supported hydroxyproline: An insoluble, recyclable organocatalyst for the asymmetric aldol reaction in water. Org. Lett. 2006, 8, 4653-4655.
28. Luo, J.;, Tan, R.;, Yu, K.;, Li, C. Y.;, Yin, D. H. Effect of additives on L-proline-catalyzed direct asymmetric aldol reactions. Chin. J. Catal. 2012, 33, 1133-1138.
29. Wang, Z.;, Yan, J.;, Zhang, X.;, Wang, L. Merrifield resin-supported ionic liquids/L-proline as efficient and recyclable catalyst systems for asymmetric aldol reaction. Synthesis 2009, 22, 3744-3750.
30. Bruckmann, A.;, Krebs, A.;, Bolm, C. Organocatalytic reactions: Effects of ball milling, microwave and ultrasound irradiation. Green Chem. 2008, 10, 1131-1141.
31. Dondoni, A.;, Massi, A. Asymmetric organocatalysis: From infancy to adolescence. Angew. Chem. Int. Ed. 2008, 47, 4638-4660.
32. Perreux, L.;, Loupy, A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 2001, 57, 9199-9223.
33. Hosseini, M.;, Stiasni, N.;, Barbieri, V.;, Kappe, C. O. Microwave-assisted asymmetric organocatalysis: A probe for nonthermal microwaveeffects and the concept of simultaneous cooling. J. Org. Chem. 2007, 72, 1417-1424.
34. Córdova, A.;, Zou, W.;, Ibrahem, I.;, Reyes, E.;, Engqvist, M.;, Liao, W. W. Acyclic amino acid-catalyzed direct asymmetric aldol reactions: Alanine, the simplest stereoselective organocatalyst. Chem. Commun. 2005, 3586-3588.