Novel binuclear chiral zirconium catalysts used in enantioselective Strecker reactions

Chirality

Volumn 12, Issue 5-6, 2000, Pages 540-543

  Kobayashi, Shu ^a   Ishitani, Haruro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Amino acid; Asymmetric catalysis; Binaphthol; Cyanation; Lewis acid; Ligand

Indexed keywords

ALDEHYDE; AMINE; HYDROGEN CYANIDE; IMINE; NITRILE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034038496     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<540::aid-chir42>3.0.co;2-p     Document Type: Article

References (24)

1. a) Shafran YM, Bakulev VA, Mokrushin VS. Synthesis and properties of α-amino nitriles. Russian Chem Rev 1989;58:148-162.
2. b) Cf. Strecker A. Üeber die künstliche Bilding der Milchsäure und einen neuen, dem Glycocoll homologen Körper. Liebigs Ann Chem 1850;75:27-45.
3. Williams RM. Synthesis of optically active α-amino acids. Oxford: Pergamon Press; 1989.
4. Williams RM, Hendrix AJ. Asymmetric synthesis of arylglycines. Chem Rev 1992;92:889-917.
5. Duthaler RO. Recent developments in the stereoselective synthesis of α-amino acids. Tetrahedron 1994;50:1539-1650.
6. Ojima I, Inaba S, Nakatsugawa K, Nagai Y. A new route to amino nitriles via cyanosilylation of Schiff bases and oximes. Chem Lett 1975;331-334.
7. Mai K, Patil G. Facile synthesis of α-amino nitriles. Tetrahedron Lett 1984;25:4583-4586.
8. Kobayashi S, Ishitani H, Ueno M. Facile synthesis of α-amino nitriles using lanthanide triflate as a Lewis acid catalyst. Synlett 1997;115-116.
9. Iyer MS, Gigstad KM, Namdev ND, Lipton M. Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptides. J Am Chem Soc 1996;118:4910-4911.
10. Sigman MS, Jacobsen EN. Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries. J Am Chem Soc 1998;120:4901-4902.
11. Sigman MS, Jacobsen EN. Enantioselective addition of hydrogen cyanide to imines catalyzed by a chiral (salen)Al(III) complex. J Am Chem Soc 1998;120:5315-5316.
12. Ishitani H, Komiyama S, Kobayashi S. Catalytic enantioselective synthesis of α-amino nitriles using a novel zirconium catalyst. Angew Chem Int Ed Engl 1998;37:3186-3188.
13. Krueger CA, Kuntz KW, Dzieba CD, Wirschum WG, Gleason JD, Snapper ML, Hoveyda AH. Ti-catalyzed enantioselective addition of cyanide to imines. A practical synthesis of optically pure α-amino acids. J Am Chem Soc 1999;121:4284-4285.
14. Corey EJ, Grogan MJ. Enantioselective synthesis of α-amino nitriles from N-benzhydryl imine and HCN with a chiral bicyclic guanidine as catalyst. Org Lett 1999;1:157-160.
15. Ishitani H, Komiyama S, Hasegawa Y, Kobayashi S. Catalytic asymmetric Strecker synthesis. Preparation of enantiomerically pure α-amino acid derivatives from aldimines and tributyltin cyanide or achiral aldehydes, amines, and hydrogen cyanide using a chiral zirconium catalyst, J Am Chem Soc 2000;122:762-766.
16. Ishitani H, Ueno M, Kobayashi S. Catalytic enantioselective Mannich-type reactions using a novel chiral zirconium catalyst. J Am Chem Soc 1997;119:7153-7154.
17. Kobayashi S, Ishitani H, Ueno M. Catalytic asymmetric synthesis of both syn-and anti-β-amino alcohols. J Am Chem Soc 1998;120:431-432.
18. Kobayashi S, Komiyama S, Ishitani H. The first catalytic enantioselective aza Diels-Alder reactions of imino dienophiles using a chiral zirconium compound. Angew Chem Int Ed Engl 1998;37:979-981.
19. Kobayashi S, Kusakabe K, Komiyama S, Ishitani H. A switch of enantiofacial selectivities using designed similar chiral ligands in zirconium-catalyzed asymmetric aza Diels-Alder reactions. J Org Chem 1999;64: 4220-4221.
20. Kobayashi S, Ishitani H. Catalytic enantioselective addition to imines. Chem Rev 1999;99:1069-1094.
21. Cox PJ, Wang W, Snieckus V. Expedient route to 3-and 3,3′-substituted 1,1′-bi-2-naphtols by directed ortho metallation and Suzuki cross coupling methods. Tetrahedron Lett 1992;33:2253-2256.
22. Kronenthal DR, Han CY, Taylor MK. Oxidative N-dearylation of 2-azetidinones. p-Anisidine as a source of azetidinone nitrogen. J Org Chem 1982;47:2765-2768.
23. Sahoo SP, Caldwell CG, Chapman KT, Durette PL, Esser CL, Kopka IE, Polo SA, Sperow KM, Nisdzwiechki LM, Izquierdo-Martin M, Chang BC, Harrison RK, Stein RL, MacCoss M, Hagmann WK. Inhibition of matrix metalloproteinases by N-carboxyalkyl dipeptides: enhanced potency and selectivity with substituted P1′ homophenylalanines. Bioorg Med Chem Lett 1995;5:2441-2446.
24. Yamada M, Nagashima N, Hasegawa J, Takahashi S. A highly efficient asymmetric synthesis of methoxyhomophenylalanine using Michael addition of phenethylamine. Tetrahedron Lett 1998;39:9019-9022.