Asymmetric cyanosilylation of aldehydes catalyzed by novel organocatalysts

Synlett

Volumn , Issue 16, 2005, Pages 2445-2448

  Wen, Yuehong ^a   Huang, Xiao ^a   Huang, Jinglun ^a   Xiong, Yan ^a   Qin, Bo ^a   Feng, Xiaoming ^a  

^a China   (China)

Author keywords

Aldehydes; Cyanosilylation; Enantioselectivity; Organocatalyst; Proline based N,N dioxide

Indexed keywords

1 NAPHTHALDEHYDE; 2 CHLOROBENZALDEHYDE; 2 NAPHTHALDEHYDE; 2 PHENYLACETALDEHYDE; 3 CHLOROBENZALDEHYDE; 3 METHOXYBENZALDEHYDE; 3 METHYLBENZALDEHYDE; 3 PHENOXYBENZALDEHYDE; 4 CHLOROBENZALDEHYDE; 4 FLUOROBENZALDEHYDE; 4 METHYLBENZALDEHYDE; ALDEHYDE DERIVATIVE; ANISALDEHYDE; BENZALDEHYDE; FURFURAL; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; SILYLATION;

EID: 26844570657     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872692     Document Type: Article

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50. Only 10% to 30% ee was obtained using the N-monoxide.
51. 3 was removed by filtration. The residue was purified by silica gel column chromatography (EtOAc) to give 1,1′-(propane-1,3-diyl)bis(N-cyclohexylpyrrolidine-2-carboxamide) (974 mg, 90%) as a white solid. For the oxidation step and stereochemistry of the N-oxide, see: O'Neil, I. A.; Miller, N. D.; Peake, J.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1993, 515.
52. +.
53. 4 and concentrated. The crude was purified by flash chromatography on silica gel (PE-EtOAc, 10:1) to yield the corresponding acetylated cyanohydrin for further analysis.