K-10-catalyzed highly diastereoselective synthesis of aziridines

Synlett

Volumn , Issue 5, 2010, Pages 745-748

  Borkin, Dmitry ^a   Carlson, Alena ^a   Török, Béla ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

Aziridines; Ethyl diazo acetate; Heterogeneous catalysis; Imines; Montmorillonite K 10

Indexed keywords

AZIRIDINE DERIVATIVE; DIAZOACETIC ACID ETHYL ESTER; ETHYL 1 (4 BROMOPHENYL) 3 PHENYLAZIRIDINE 2 CARBOXYLATE; ETHYL 1 (4 CYANOPHENYL) 3 PHENYLAZIRIDINE 2 CARBOXYLATE; ETHYL 1 PHENYL 3 (2 TOLYL)AZIRIDINE 2 CARBOXYLATE; IMINE; MONTMORILLONITE; MONTMORILLONITE K 10; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION TIME; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 77749293065     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219361     Document Type: Article

References (14)

1. Somfai P, Ahman J, Targets Heterocycl. Syst. 1999 3 341, Zwanenburg B, tenHolte P, Top. Curr. Chem. 2001 216 93, Sweeney J B., Chem. Soc. Rev. 2002 31 247, Schramm H, Pavlova M, Hoenke C, Christoffers J, Synthesis 2009 1659 For review, see:, Singh G S., Dhooghe M, DeKimpe N, Chem. Rev. 2007 107 2080
2. Ismail F M. D., Levitsky D O., Dembitsky V M., Eur. J. Med. Chem. 2009 44 3373, Yudin A K., Aziridines and Epoxides in Organic Synthesis Wiley-VCH Weinheim 2006
3. Ali H E., Tenside, Surfactants, Deterg. 2008 45 76, Degel B, Staib P, Rohrer S, Scheiber J, Martina E, Buechold C, Baumann K, Morschhaeuser J, Schirmeister T, ChemMedChem 2008 3 302, Ponte-Sucre A, Vicik R, Schultheis M, Schirmeister T, Moll H, Antimicrob. Agents Chemother. 2006 50 2439
4. Padwa A, Flick A C., Leverett C A., Stengel T, J. Org. Chem. 2004 69 6377, Kantam M L., Neeraja V, Kavita B, Haritha Y, Synlett 2004 525, Vyas R, Gao G.-Y, Harden J D., Zhang X P., Org. Lett. 2004 6 1907, Subbarayan V, Ruppel J V., Zhu S, Perman J A., Zhang X P., Chem. Commun. 2009 4266
5. Rasmussen K G., Jørgensen K A., J. Chem. Soc., Chem. Commun. 1995 34 676, Xie W, Fang J, Li J, Wang P G., Tetrahedron 1999 55 12929, Yadav J S., Reddy B V. S., SheshaRao M, Reddy P N., Tetrahedron Lett. 2003 44 5275, Casarrubios L, Perez J A., Brookhart M, Templeton J L., J. Org. Chem. 1996 61 8358
6. Zhu Z, Espenson J H., J. Org. Chem. 1995 60 7090, Li Y, Chan P W. H., Zhu N, Che C, Kwong H, Organometallics 2004 23 54, Redlich M, Hossain M M., Tetrahedron Lett. 2004 45 8987
7. Yadav J S., Reddy B V. S., Reddy P N., SheshaRao M, Synthesis 2003 1387
8. Corma A, Chem. Rev. 1995 95 559, Gates B C., Catalysis by Solid Acids, In Encyclopedia of Catalysis Vol. 2, Horváth I, Wiley New York 2003 104, Yip A C. K., Lam F L. Y., Hu X J., Chem. Commun. 2005 3218, Dasgupta S, Török B, Curr. Org. Synth. 2008 5 321
9. Abid M, Landge S M., Török B, Org. Prep. Proced. Int. 2006 35 495, Abid M, Spaeth A, Török B, Adv. Synth. Catal. 2006 348 2191, Landge S M., Atanassova V, Thimmaiah M, Török B, Tetrahedron Lett. 2007 48 5161, Dasgupta S, Török B, Org. Prep. Proced. Int. 2008 40 1
10. Balogh M, Laszlo P, Organic Chemistry Using Clays Springer Berlin 1993, Varma R S., Tetrahedron 2002 58 1235, Polshettiwar V, Varma R S., Acc. Chem. Res. 2008 41 629
11. Williams A L., Johnston J N., J. Am. Chem. Soc. 2004 126 1612
12. Zhou Y.-L, Chin. J. Chem. 2007 25 422
13. Krumper J R., Gerisch M, Suh J M., Bergman R G., Tilley T D., J. Org. Chem. 2003 68 9705
14. Mayer M F., Wang Q, Hossain M M., J. Organomet. Chem. 2001 630 78