Synthesis of Chiral NADH Analog Based on Proline Template Including Thiourea and Nicotinic Acid Moieties

REFERENCES

• (a) Saini , A. ; Kumar , S. ; Sandhu , J. S. Hantzsch reaction: Recent advances in Hantzsch 1,4-dihydropyridines . J. Sci. Ind. Res. 2008 , 67 , 95 ; (b) Connon , S. J. Asymmetric organocatalytic reductions mediated by dihydropyridines . Org. Biomol. Chem. 2007 , 5 , 3407 .
   Web of Science ®Google Scholar
• Wang , N. X. ; Zhao , J. A novel NADH model: Design, synthesis, and its chiral reduction and fluorescent emission . Adv. Synth. Catal. 2009 , 351 , 3045 , and references cited therein .
   Google Scholar
• Dalko , P. I. Enantioselective Organocatalysis ; Wiley-VCH : Weinheim , 2007 .
   Google Scholar
• Procuranti , B. ; Connon , S. J. Asymmetric catalysis with bifunctional cinchona alkaloid-based urea- and thiourea organocatalysts . Chem. Commun. 2007 , 1421 .
   Google Scholar
• (a) Doyle , A. G. ; Jacobsen , E. N. Small-molecule H-bond donors in asymmetric catalysis . Chem. Rev. 2007 , 107 , 5713 ; (b) Connon , S. J. The design of novel, synthetically useful (thio)urea-based organocatalysts . Synlett. 2009 , 354 .
   PubMed Web of Science ®Google Scholar
• (a) Menche , D. ; Arikan , F. Thiourea-catalyzed direct reductive amination of aldehydes . Synlett. 2006 , 841 ; (b) Zhang , Z. ; Schreiner , P. R. Thiourea-catalyzed transfer hydrogenation of aldimines . Synlett. 2007 , 1455 .
   Google Scholar
• Dahlin , N. ; Boegevig , A. ; Adolfsson , H. N-Arenesulfonyl-2-aminomethylpyrrolidines—Novel modular ligands and organocatalysts for asymmetric catalysis . Adv. Synth. Catal. 2004 , 346 , 1101 – 1105 .
   Web of Science ®Google Scholar
• Ballestaz , J. ; Lelieveld , P. ; Ottenheijm , H. The role of the hydroxymethyl function on the biological activity of the antitumor antibiotic sparsomycin . Eur. J. Med. Chem. 1989 , 24 , 503 .
   Google Scholar
• Bellis , E. ; Vasilatou , K. ; Kokotos , G. 4-Substituted prolyl sulfonamides as enantioselective organocatalysts for aldol reactions . Synthesis 2005 , 14 , 2407 .
   Google Scholar
• Lin , W. ; Zhang , X. ; He , Z. ; Jin , Y. ; Gong , L. ; Mi , A. Reduction of azides to amines or amides with zinc and ammonium chloride as reducing agent . Synth. Commun. 2002 , 32 , 3279 .
   Web of Science ®Google Scholar
• Bose , D. ; Thurston , D. Boron trifluoride–promoted cleavage of benzyl carbamates . Tetrahedron Lett. 1990 , 31 , 6903 .
   Google Scholar
• Ihara , M. ; Taniguchi , N. ; Nogochi , K. ; Fujumoto , K. ; Kametani , T. Total synthesis of hydrocinchonidine and hydrocinchonine via photo-oxygenation of an indole derivative . J. Chem. Soc., Perkin Trans. 1 1988 , 1277 .
   Google Scholar
• Nudelman , A. ; Bechor , Y. ; Falb , E. ; Fischer , B. ; Vexler , B. A. ; Nudelman , A. Acetyl chloride-methanol as a convenient reagent for (a) quantitative formation of amine hydrochlorides, (b) carboxylate ester formation, (c) mild removal of N-t-Boc-protective group . Synth. Commun. 1998 , 28 , 471 .
   Web of Science ®Google Scholar
• Cao , C.-L. ; Ye , M.-C. ; Sun , X.-L. ; Tang , Y. Pyrrolidine−thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins . Org. Lett. 2006 , 8 , 2901 .
   PubMed Web of Science ®Google Scholar
• Van Es , T. ; Backeberg , O. G. A new synthesis of para-substituted benzils, and preparation of some of the corresponding benxoins . J. Chem. Soc. 1963 , 1371 .
   Google Scholar