Pyrrolidine-catalyzed condensation of ethyl diazoacetate to aldehydes in water

Synthetic Communications

Volumn 40, Issue 12, 2010, Pages 1724-1729

  Kantam, M Lakshmi ^a   Chakrapani, L ^a   Ramani, T ^a   Reddy, K Rajender ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

A diazo carbonyl compounds; Aldol type reaction; Ethyl diazoacetate; Pyrrolidine; Water

Indexed keywords

ACETONITRILE; ALDEHYDE; BENZALDEHYDE DERIVATIVE; DIAZOACETIC ACID ETHYL ESTER; DICHLOROMETHANE; DIMETHYL ETHER; ETHER; METHANOL; MORPHOLINE; PIPERIDINE; PROLINE; PYRROLIDINE DERIVATIVE; SOLVENT; TETRAHYDROFURAN; WATER;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; POLYMERIZATION; PROCESS OPTIMIZATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 77952568974     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003794517     Document Type: Article

References (31)

1. Doyle, M. P.; Mckervey, M. A. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998.
2. (a) Taber, D. F.; Petty, E. H. General route to highly functionalized cyclopentane derivatives by intramolecular C-H insertion. J. Org. Chem. 1982, 47, 4808-4809;
3. (b) Hashimoto, S.; Watanabe, N.; Ikegami, S. Highly selective insertion into aromatic C-H bonds in rhodium(II) triphenylacetate-catalysed decomposition of a-diazocarbonyl compounds. J. Chem. Soc. Chem. Commun. 1992, 1508-1510;
4. (c) Davies, M. J.; Moody, C. J.; Taylor, R. J. Rhodium carbenoid-mediated cyclizations, part 7: Synthesis and coupling reactions of 2-substituted 3-oxooxepanes. J. Chem. Soc., Perkin Trans. 1991, 1, 1-7;
5. (d) Miller, D. J.; Moody, C. J. Synthetic applications of the O-H insertion reactions of carbenes and carbenoids derived from diazocarbonyl and related diazo compounds. Tetrahedron 1995, 51, 10811-101843;
6. (e) Calter, M. A.; Sugathapala, P. M.; Zhu, C. Aldol cyclization reaction sequence for the synthesis of tetrahydrofurans. Tetrahedron Lett. 1997, 38, 3837-3840.
7. (a) Horton, D.; Philips, K. D. Synthesis of methyl 2-deoxy-2-diazo-D- arabino-hexonate, its behaviour on photolysis and thermolysis, and conversion into a pyrazole derivative. Carbohydr. Res. 1972, 22, 151-162;
8. (b) Wenkert, E.; Ceccherelli, P.; Fugiel, R. A. a-Diazo-b- hydroxycarboxylates. J. Org. Chem. 1978, 43, 3982-3983;
9. (c) Taylor, K. G. Carbenes and carbenoids with neighboring heteroatoms. Tetrahedron 1982, 38, 2751-2772;
10. (d) Nickon, A. New perspectives on carbene rearrangements: Migratory aptitudes, bystander assistance, and geminal efficiency. Acc. Chem. Res. 1993, 26, 84-89.
11. Pellicciari, R.; Natalini, B.; Ceccheti, S.; Fringnelli, R. An efficient procedure for the regiospecific preparation of D-homo-steroid derivatives. Steroids 1987, 49, 433-441.
12. (a) Schollkopf, U.; Frasnelli, H.; Hoppe, D. Ethyl 2-oxazoline-5- carboxylate from ethyl isocyanoacetate and carbonyl compounds. Angew. Chem., Int. Ed. Engl. 1970, 9, 300-301;
13. (b) Moody, C. J.; Taylor, R. J. Rhodium carbenoid-mediated cyclizations: Use of ethyl lithiodiazoacetate in the preparation of x-hydroxy-,-mercapto-, and-boc-amino-a-diazo-b-keto esters. Tetrahedron Lett. 1987, 28, 5351-5352;
14. (c) Jiang, N.; Qu, Z.; Wang, J. 1,2-Aryl and 1,2-hydride migration in transition metal complex-catalyzed diazo decomposition: A novel approach to a-aryl-b-enamino esters. Org. Lett. 2001, 3, 2989-2992;
15. (d) Wenkert, E.; McPherson, A. A. Condensations of acyldiazomethanes with aldehydes, ketones, and their derivatives. J. Am. Chem. Soc. 1972, 94, 8084-8090;
16. (e) Jiang, N.; Wang, J. DBU-promoted condensation of acyldiazomethanes to aldehydes and imines under catalytic conditions. Tetrahedron Lett. 2002, 43, 1285-1287;
17. (f) Wang, J.; Yao, W. Base-induced heterochiral dimerization of an oxiranyl carbaldimine: Stereoselective synthesis of a highly functionalized aziridine. Org. Lett. 2003, 3, 1527-1530;
18. (g) Varala, R.; Ramu, E.; Sreelatha, N.; Rao, A. S. Catalytic aldol-type reaction of aldehydes with ethyl diazoacetate using quarternary ammonium hydroxide as the base. Tetrahedron Lett. 2006, 47, 877-880.
19. (a) Guillena, G.; Ramón, D. J. Enantioselective a-heterofunctionalisation of carbonyl compounds: Organocatalysis is the simplest approach. Tetrahedron: Asymmetry 2006, 17, 1465-1492;
20. (b) Dalko, P. I.; Moisan, L. In the golden age of organocatalysis. Angew. Chem., Int. Ed. 2004, 43, 5138-5175;
21. (c) Duthaler, R. O. Proline-catalyzed asymmetric a-amination of aldehydes and ketones: An astonishingly simple access to optically active a-hydrazino car-bonyl compounds. Angew. Chem., Int. Ed. 2003, 42, 975-978;
22. (d) Jarvo, E. R.; Miller, S. J. Amino acids and peptides as asymmetric organocatalysts. Tetrahedron 2002, 58, 2481-2495;
23. (e) Berkessel, A.; Groger, H. (Eds.). Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH: Weinheim, 2005.
24. (a) Dickerson, T. J.; Janda, K. D. Aqueous aldol catalysis by a nicotine metabolite. J. Am. Chem. Soc. 2002, 124, 3220-3221;
25. (b) Cordova, A.; Notz, W.; Barbas, C. F. III. Direct organocatalytic aldol reactions in buffered aqueous media. Chem. Commun. 2002, 3024-3025;
26. (c) Reymond, J.-L.; Chen, Y. Catalytic, enantioselective aldol reaction with an artificial aldolase assembled from a primary amine and an antibody. J. Org. Chem. 1995, 60, 6970-6979;
27. (d) Dickerson, T. J.; Lovell, T.; Meijler, M. M.; Noodleman, L.; Janda, K. D. Nornicotine aqueous aldol reactions: Synthetic and theoretical investigations into the origins of catalysis. J. Org. Chem. 2004, 69, 6603-6609.
28. (a) Ramachary, D. B.; Barbas III, C. F. Towards organo-click chemistry: Development of organocatalytic multicomponent reactions through combinations of aldol, Wittig, Knoevengel, Michael, Diels-Alder, and Huisgen cycloaddition reactions. Chem. Eur. J. 2004, 10, 5323-5331;
29. (b) Ji, C.; Peng, Y.; Huang, C.; Wang, N.; Luo, Z.; Jiang, Y. An efficient method for direct aldol reactions catalyzed by pyrrolidine=catechol: The influence of cooperation of Brønsted acidity and hydrogen bond on the reaction. J. Mol. Catal. A: Chem. 2006, 246, 136-139;
30. (c) Wang, J.; Li, H.; Lou, B.; Zu, L.; Guo, H.; Wang, W. Enantio-and diastereoselective Michael addition reactions of unmodified aldehydes and ketones with nitroolefins catalyzed by a pyrrolidine sulfonamide. Chem. Eur. J. 2006, 12, 4321-4322.
31. Chimni, S. S.; Mahajan, D. Electron deficiency of aldehydes controls the pyrrolidine-catalyzed direct cross-aldol reaction of aromatic=heterocyclic aldehydes and ketones in water. Tetrahedron 2005, 61, 5019-5025.