One-Pot, Two-Step Direct Conversion of Alkenes to Amines Through Tandem Ozonolysis and Ammonia-Borane in Water

REFERENCES

• 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 .
   Web of Science ®Google Scholar
• Tarasevich , V. A. ; Kozlov , N. G. Reductive amination of oxygen-containing organic compounds . Russ. Chem. Rev. 1999 , 68 , 55 .
   Google Scholar
• Ghosh , A. K. ; Bilcer , G. ; Schiltz , G. Synthesis of FDA-approved HIV protease inhibitors . Synthesis 2001 , 15 , 2203 .
   Google Scholar
• Van Ornum , S. G. ; Champeau , R. M. ; Pariza , R. Ozonolysis application in drug synthesis . Chem. Rev. 2006 , 106 , 2990 .
   PubMed Web of Science ®Google Scholar
• (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 ; (b) Lavalle , P. ; Bouthillier , G. Efficient conversion of (1R, 5R)-(+)-α-pinene to (1S, 5R)-(−) nopinone . J. Org. Chem. 1986 , 51 , 1362 .
   PubMed Web of Science ®Google Scholar
• (a) Fisher , T. J. ; Dussault , P. H. Fragmentation of chloroperoxides: Hypochlorite- mediated dehydration of hydroperoxyacetals to esters . Tetrahedron Lett. 2010 , 51 , 5615 ; (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 .
   PubMed Web of Science ®Google Scholar
• Baxter , E. W. ; Reitz , A. B. Reductive amination of carbonyl compounds with borohydride and borane reducing agents . Org. React. 2002 , 59 , 1 .
   Google Scholar
• (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; (b) Abdel-Magid , A. F. ; Carson , K. C. ; Harris , B. D. ; Maryanoff , C. A. ; Shah , R. D. Reductive amination of aldehydes and ketones with NaBH (OAc)3: Studies on direct and indirect reductive amination procedures. J. Org. Chem. 1996, 61, 3849.
   Web of Science ®Google Scholar
• Gribble , G. Sodium borohydride in carboxylic acid media: A phenomental reduction system . Chem. Soc. Rev. 1998 , 27 , 395 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• (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 ; (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 ; (c) Kawaguchi , M. ; Hayashi , O. ; Sakai , N. ; Hamada , M. ; Yamamoto , Y. ; Oda , J. J. Agric. Biol. Chem. 1986 , 50 , 3107 ; (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 ; (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 .
   Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• Pollart , K. A. ; Miller , R. E. Ozonolysis-reductive amination of olefins . J. Org. Chem. 1962 , 27 , 2392 .
   Web of Science ®Google Scholar
• Borch , R. F. ; Hassid , A. I. New method for the methylation of amines . J. Org. Chem. 1972 , 37 , 1673 .
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Bunnelle , W. H. Preparation, properties, and reactions of carbonyl oxides . Chem. Rev. 1991 , 91 , 335 .
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Schwartz , C. ; Raible , J. ; Mott , K. ; Dussault , P. H. Reductive ozonolysis via a new fragmentation of carbonyl oxides . Tetrahedron 2006 , 62 , 10747 .
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar