One-pot, two-step direct conversion of alkenes to amines through tandem ozonolysis and ammonia-borane in water

Synthetic Communications

Volumn 44, Issue 4, 2014, Pages 493-499

  Tyagi, Vipin ^a   Gupta, Ashok Kumar ^a  

^a S S v College   (India)

Author keywords

Alkenes; amines; ammonia borane; ozone; water

Indexed keywords

ALKENE; AMINE; AMMONIA; BORANE DERIVATIVE; REDUCING AGENT; WATER;

AMINATION; ARTICLE; BIOTRANSFORMATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; ONE POT SYNTHESIS; OZONOLYSIS;

EID: 84891822349     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.815216     Document Type: Article

References (36)

1. Robichaud, A.;, Ajjou, A. First example of direct reductive amination of aldehydes with primary and secondary amines catalyzed by water-soluble transition metal catalysts. Tetrahedron Lett. 2006, 47, 3633.
2. Tarasevich, V. A.;, Kozlov, N. G. Reductive amination of oxygen-containing organic compounds. Russ. Chem. Rev. 1999, 68, 55.
3. Ghosh, A. K.;, Bilcer, G.;, Schiltz, G. Synthesis of FDA-approved HIV protease inhibitors. Synthesis 2001, 15, 2203.
4. Van Ornum, S. G.;, Champeau, R. M.;, Pariza, R. Ozonolysis application in drug synthesis. Chem. Rev. 2006, 106, 2990.
5. (a), Chen, L.;, Wiemer, D. F. Synthesis of a carbon analogue of N-acetylmannosamine via acetolysis on a relatively stable ozonide. J. Org. Chem. 2002, 67, 7561;
6. (b), Lavalle, P.;, Bouthillier, G. Efficient conversion of (1R, 5R)-(+)-α-pinene to (1S, 5R)-(-) nopinone. J. Org. Chem. 1986, 51, 1362.
7. (a), Fisher, T. J.;, Dussault, P. H. Fragmentation of chloroperoxides: Hypochlorite-mediated dehydration of hydroperoxyacetals to esters. Tetrahedron Lett. 2010, 51, 5615;
8. (b), Schiaffo, C. E.;, Dussault, P. H. Ozonolysis in solvent/water mixture: Direct conversion of alkenes to aldehydes and ketones. J. Org. Chem. 2008, 73, 4688.
9. Baxter, E. W.;, Reitz, A. B. Reductive amination of carbonyl compounds with borohydride and borane reducing agents. Org. React. 2002, 59, 1.
10. (a), Abdel-Magid, A. F.;, Mehrman, S. J. A review on the use of sodium triacetoxyborohydride in the reductive amination of ketones and aldehydes. Org. Process Res. Dev. 2006, 10, 971;
11. 3: Studies on direct and indirect reductive amination procedures. J. Org. Chem. 1996, 61, 3849.
12. Gribble, G. Sodium borohydride in carboxylic acid media: A phenomental reduction system. Chem. Soc. Rev. 1998, 27, 395.
13. Branch, C. L. Preparation of 1,2,3,4,-tetrahydroisoquinolines lacking electron-donating groups-An intramolecular cyclization complementary to the Picket-Spengler reaction. Tetrahedron Lett. 1996, 37, 5453.
14. Payack, J. F.;, Vazques, E.;, Matty, L.;, Kress, M. H.;, McNamara, J. A concise synthesis of a novel antiongiogenic tyrosine kinase inhibitor. J. Org. Chem. 2005, 70, 175.
15. Ripin, D. H. B.;, Abele, S.;, Cai, W.;, Blumenkopf, T.;, Casavant, J. M.;, Doty, J. L.;, Flanagan, M.;, Koecher, C.;, Laue, K. W.;, Wilcox, G. Developemt of a scaleable route for the production of cis-N-benzyl-3- methylamino-4-methylpiperidine. Org. Proc. Res. Dev. 2003, 7, 115.
16. (a), White, W. R.;, King, W. S.;, O'Brien, L. J. Catalytic reduction of ozonides, II: Synthesis of amines from olefins. Tetrahedron Lett. 1971, 39, 3591;
17. (b), Shawe, T. T.;, Sheils, C. J.;, Gray, S. M.;, Conard, J. L. Iterative reductive alkylation approach to alkaloids: A synthesis of (+)-monomorine I and its C-3 epimer. J. Org. Chem. 1994, 59, 5841;
18. (c), Kawaguchi, M.;, Hayashi, O.;, Sakai, N.;, Hamada, M.;, Yamamoto, Y.;, Oda, J. J. Agric. Biol. Chem. 1986, 50, 3107;
19. (d), Diaper, D. G. M.;, Mitchell, D. L. Reactions of ozonides, II: Reductive amination of ozonization products with ethanolic ammonia. Can. J. Chem. 1962, 40, 1189;
20. (e), Brooks, P. R.;, Caron, S.;, Singer, R. A. Synthesis of 2,3,4,5-Tetrahydro-1,5-methano-1H-3-benzazepine via oxidative cleavage and reductive amination strategies. Synthesis 2004, 11, 1755.
21. Laventine, D. M.;, Davies, M.;, Evinson, E. L.;, Jenkins, P. R.;, Cullis, P. M.;, Fawcett, J. Ring-closing double reductive amination route to aza-heteroanuulated sugars. Tetrahedron Lett. 2005, 46, 307.
22. Hon, Y. S.;, Lu, L. The reaction of the ozonides with secondary amines: An efficient and novel way to prepare tertiary amine from mono-and 1,1-di-substituted alkenes via corresponding ozonides. Tetrahedron Lett. 1993, 34, 5309.
23. Pollart, K. A.;, Miller, R. E. Ozonolysis-reductive amination of olefins. J. Org. Chem. 1962, 27, 2392.
24. Borch, R. F.;, Hassid, A. I. New method for the methylation of amines. J. Org. Chem. 1972, 37, 1673.
25. Yang, L.;, Butora, G.;, Jiao, R. X.;, Pasternak, A.;, Zhou, C.;, Parsons, W. H.;, Mills, S. G. Discovery of 3-piperidinyl-1-cyclopentanecarboxamide as a novel scaffold for highly potent CC chemokine receptor 2 antagonists. J. Med. Chem. 2007, 50, 2609.
26. Ishmuratov, G. Y.;, Kharisov, R. Y.;, Yakovleva, M. O.;, Botsman, O. V.;, Muslukhov, R. R.;, Tolstikov, G. A. Ozonolysis of alkenes and study of reactions of polyfunctional compounds, LXIII: A new procedure for direct reduction of 1-methylcycloalkene ozonolysis products to hydroxyketones. Russ. J. Org. Chem. 2001, 37, 37.
27. Bunnelle, W. H. Preparation, properties, and reactions of carbonyl oxides. Chem. Rev. 1991, 91, 335.
28. Zmitek, K.;, Zupan, M.;, Iskra, J. α-Substituted organic peroxides: synthetic strategies for a biologically important class of gem-dihydroperoxide and perketal derivatives. Org. Biomol. Chem. 2007, 5, 3895.
29. Kyasa, S. K.;, Fisher, T. J.;, Dussault, P. H. A mild one-pot conversion of alkenes into amines through tandem ozonolysis and reductive amination. Synthesis 2011, 21, 3475.
30. Charnley, R. W.;, Fisher, T. J.;, Johnson, B. M.;, Dussault, P. H. Pyridine is an organocatalyst for the reductive ozonolysis of alkenes. Org. Lett. 2012, 14, 2242.
31. Schwartz, C.;, Raible, J.;, Mott, K.;, Dussault, P. H. Reductive ozonolysis via a new fragmentation of carbonyl oxides. Tetrahedron 2006, 62, 10747.
32. Tajbakhsh, M.;, Hosseinzadeh, R.;, Heydari, A. Catalyst-free one reductive alkylation of primary and secondary amines and N,N-dimethylation of amino acids using sodium borohydride in 2,2,2,-trifluoroethanol. Synthesis 2011, 3, 490.
33. Bagal, D. B.;, Watile, R. A.;, Khedkar, M. V. PS-Pd-NHC: An efficient and heterogeneous recyclable catalyst for direct reductive amination of carbonyl compounds with primary/secondary amines in aqueous medium. Catal. Sci. Technol. 2012, 2, 354.
34. Byun, E.;, Hong, B.;, Rhee, H. One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes. J. Org. Chem. 2007, 72, 9815.
35. Sreedhar, B.;, Reddy, P. S.;, Devi, D. K. Direct one-pot reductive amination of aldehydes with nitroarenes in a domino fashion: Catalysis by gum-acacia-stabilized palladium nanoparticles. J. Org. Chem. 2009, 74, 8806.
36. Liao, W.;, Chen, Y.;, Liu, Y.;, Duan, H. 1,2,3-Triazole-borane: Stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water. Chem. Commun. 2009, 6436.