Catalytic enantioselective Strecker reaction of ketoimines

Journal of the American Chemical Society

Volumn 125, Issue 19, 2003, Pages 5634-5635

  Masumoto, Shuji ^a   Usuda, Hiroyuki ^a   Suzuki, Masato ^a   Kanai, Motomu ^a,b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; CATECHOL; IMINE; KETONE DERIVATIVE; LANTHANIDE; LEWIS ACID; NITRILE;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CYANATION; ENANTIOSELECTIVITY; ESTERIFICATION; HYDROLYSIS;

CATALYSIS; CYANIDES; GADOLINIUM; IMINES; ORGANOMETALLIC COMPOUNDS; PHOSPHINES; STEREOISOMERISM;

EID: 0037958740     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034980+     Document Type: Article

References (32)

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24. (b) Yabu, K.; Masumoto, S.; Kanai, M.; Curran, D. P.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 2923. Chiral ligands 1 and 3 can be synthesized through 12 steps from triacetyl-D-glucose (ca. 20% overall yield, not optimized), and are commercially available from Junsei Chemical Co., Ltd. (Fax: +81-3-3270-5461).
25. For the beneficial effects of protic additives on catalytic enantioselective Strecker reaction of aldoimines, see refs 1h, 1j, 11, and 1m.
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27. Krzyzanowska, B.; Stec, W. J. Synthesis 1982, 270. For a recent example of catatlytic enantioselective reaction (hydrogenation) using N-diphenylphosphinoyl ketoimines, see; Spindler, F.; Blaser, H.-U. Adv. Synth. Catal. 2001, 343, 68.
28. The product appeared to be silylated 5 in the reaction mixture. The silyl ether was hydrolyzed during the aqueous workup.
29. 3 (0.2 M in THF, 37.5 μL, 0.0075 mmol, purchased from Kojundo Chemical Laboratory Co., Ltd. Fax: +81-492-84-1351) was added to a solution of ligand 3 (7.5 mg, 0.015 mmol) in 0.15 mL of THF in an ice bath. The mixture was stirred for 30 min at 45°C, and then the solvent was evaporated. After drying the resulting pre-catalyst under vacuum (∼5 mmHg) for 1 h, substrate 4a (96 mg, 0.3 mmol) was added as a solid in one portion. Propionitrile (0.1 mL) and TMSCN (60 μL, 0.45 mmol) were added to the mixture at -40°C to start the reaction.
30. On the basis of the NMR studies, imines 4 appear to exist in a very fast equilibrium between E and Z isomers. See the Supporting Information for details.
31. Formylation was necessary for further conversion of the N-benzyl-protected aminonitriles to the deprotected amino acid derivatives, due to their lability. See ref 2.
32. The crude mixture after workup contains product 5, ligand 3, and the silylated ligand. The ligand was recoverable after acid hydrolysis in 83% yield.