Scalable organocatalytic asymmetric Strecker reactions catalysed by a chiral cyanide generator

Nature Communications

Volumn 3, Issue , 2012, Pages

  Yan, Hailong ^a   Suk Oh, Joong ^a   Lee, Ji Woong ^a,b   Eui Song, Choong ^a  

^a Sungkyunkwan University   (South Korea)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; CYANIDE; MACROGOL; NITRILE; SULFONE;

AMINO ACID; CATALYST; SUBSTRATE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PHENOMENA; CHEMICAL REACTION; ENANTIOSELECTIVITY; ONE POT SYNTHESIS; STRECKER REACTION;

EID: 84870832351     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms2216     Document Type: Article

References (33)

1. Hughes, A. B. Amino Acids, Peptides and Proteins in Organic Chemistry (Wiley-VCH, Weinheim, 2009).
2. Ma, J. S. Unnatural a-amino acids in drug discovery. Chim. Oggi 21, 65-68 (2003).
3. Strecker, A. Über die künstliche Bildung der Milchsäure und einen neuen, dem Glycocoll homologen Körper. Justus Liebigs Ann. Chem. 75, 27-45 (1850).
4. Duthaler, R. O. Recent developments in the stereoselective synthesis of alpha-amino acids. Tetrahedron 50, 1539-1650 (1994).
5. Bommarius, A. S., Schwarm, M. & Drauz, K. Comparison of different chemoenzymatic process routes to enantiomerically pure amino acids. Chimia 55, 50-59 (2001).
6. Breuer, M. et al. Industrial methods for the production of optically active intermediates. Angew. Chem. Int. Ed. 43, 788-824 (2004).
7. Najera, C. & Sansano, J. M. Catalytic asymmetric synthesis of alpha-amino acids. Chem. Rev. 107, 4584-4671 (2007).
8. Yet, L. Recent developments in catalytic asymmetric Strecker-type reactions. Angew. Chem. Int. Ed. 40, 875-877 (2001).
9. Gröger, H. Catalytic enantioselective Strecker reactions and analogous syntheses. Chem. Rev. 103, 2795-2827 (2003).
10. Spino, C. Recent developments in the catalytic asymmetric cyanation of ketimines. Angew. Chem. Int. Ed. 43, 1764-1766 (2004).
11. Shibasaki, M., Kanai, M. & Mita, T. The catalytic asymmetric Strecker reaction. Org. React. 70, 1-119 (2008).
12. Connon, S. J. The catalytic asymmetric strecker reaction: ketimines continue to join the fold. Angew. Chem. Int. Ed. 47, 1176-1178 (2008).
13. Merino, P., Marques-Lopez, E., Tejero, T. & Herrera, R. P. Organocatalyzed Strecker reactions. Tetrahedron 65, 1219-1234 (2009).
14. Martens, J. Enantioselective organocatalytic Strecker reactions in the synthesis of alpha-amino acids. ChemCatChem 2, 379-381 (2010).
15. Wang, J., Liu, X. & Feng, X. Asymmetric Strecker reactions. Chem. Rev. 111, 6947-6983 (2011).
16. Ooi, T., Uematsu, Y. & Maruoka, K. Asymmetric Strecker reaction of aldimines using aqueous potassium cyanide by phase-transfer catalysis of chiral quaternary ammonium salts with a tetranaphthyl backbone. J. Am. Chem. Soc. 128, 2548-2549 (2006).
17. Zuend, S. J., Coughlin, M. P., Lalonde, M. P. & Jacobsen, E. N. Scaleable catalytic asymmetric Strecker syntheses of unnatural alpha-amino acids. Nature 461, 968-970 (2009).
18. Banphavichit, V., Mansawat, W., Bhanthumnavin, W. & Vilaivan, T. A practical synthesis of optically active arylglycines via catalytic asymmetric Strecker reaction. Tetrahedron 65, 5849-5854 (2009).
19. Lee, J. W. et al. Bis-terminal hydroxy polyethers as all-purpose, multifunctional organic promoters: a mechanistic investigation and applications. Angew. Chem. Int. Ed. 48, 7683-7686 (2009).
20. Jadhav, V. H. et al. Oligoethylene glycols as highly efficient mutifunctional promoters for nucleophilic-substitution reactions. Chem. Eur. J. 18, 3918-3924 (2012).
21. Yan, H. et al. A chiral anion generator: application to catalytic desilylative kinetic resolution of silyl-protected secondary alcohols. Angew. Chem. Int. Ed. 49, 8915-8917 (2010).
22. Engberts, J. B. & Strating, J. Mannich condensation of sulfinic acids, aldehyde and ethyl carbamate 2. Use of higher aldehydes. Recl. Trav. Chim. Pays-Bas 84, 942-950 (1965).
23. Petrini, M. Alpha-amido sulfones as stable precursors of reactive N-acylimino derivatives. Chem. Rev. 105, 3949-3977 (2005).
24. Yin, B. L., Zhang, Y. X. & Xu, L. W. Recent applications of alpha-amido sulfones as in situ equivalents of activated imines for asymmetric catalytic nucleophilic addition reactions. Synthesis 3583-3595 (2010).
25. Yang, J. W., Pan, S. C. & List, B. Synthesis of tert-butyl (1S,2S)-2-methyl-3-oxo-1-phenylpropylcarbamate by asymmetric Mannich reaction. Org. Synth. 86, 11-17 (2009).
26. Banphavichit, V., Chaleawlertumpon, S., Bhanthumnavin, W. & Vilaivan, T. A convenient synthesis of N-boc-protected alpha-aminonitriles from alpha-amidosulfones. Synth. Commun. 34, 3147-3160 (2004).
27. Herrera, R. P., Sgarzani, V., Bernardi, L., Fini, F., Pettersen, D. & Ricci, A. Phase transfer catalyzed enantioselective Strecker reactions of a-amido sulfones with cyanohydrins. J. Org. Chem. 71, 9869 (2006).
28. Ooi, T., Uematsu, Y., Fujimoto, J., Fukumoto, K. & Maruoka, K. Advantage of in situ generation of N-arylsulfonyl imines from a-amide sulfones in the phase-transfer-catalyzed asymmetric Strecker reaction. Tetrahedron Lett. 48, 1337-1340 (2007).
29. Reingruber, R., Baumann, T., Dahmen, S. & Bräse, S. Use of the chiral pool-practical asymmetric organocatalytic Strecker reaction with quinine. Adv. Synth. Cat. 351, 1019-1024 (2009).
30. Li, W. & Lam, Y. Solid-phase synthesis of 3,4-dihydro-1H-pyrimidine- 2-ones using sodium benzenesulfinate as a traceless linker. J. Comb. Chem. 7, 721-725 (2005).
31. Amstrong, A., Edmonds, I. D., Swarbrick, M. E. & Treweeke, N. R. Electrophilic amination of enolates with oxaziridines: effects of oxaziridine structure and reaction conditions. Tetrahedron 61, 8423-8442 (2005).
32. Seayad, A. M., Ramalingam, B., Yoshinaga, K., Nagata, T. & Chai, C. L. L. Highly enantioselective titanium-catalyzed cyanation of imines at room temperature. Org. Lett. 12, 264-267 (2010).
33. Hashimoto, T., Kimura, H. & Maruoka, K. Axially chiral dicarboxylic acid-catalyzed asymmetric imino aza-enamine reaction/oxidation as a Strecker reaction surrogate. Tetrahedron: Asymmetry 21, 1187-1188 (2010).