Highly enantioselective cyanosilylation of aldehydes catalyzed by a chiral oxazaborolidinium ion

Journal of the American Chemical Society

Volumn 126, Issue 26, 2004, Pages 8106-8107

  Ryu, Do Hyun ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; OXAZABOROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHIRALITY; COMPLEX FORMATION; CYANOSILYLATION; CYCLOADDITION; ENANTIOSELECTIVITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SILYLATION;

EID: 3042770462     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0475959     Document Type: Article

References (37)

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37. 2. Then, TMSCN (0.752 mL, 5.64 mmol) was added followed by the aldehyde (5 mmol, dropwise) in 3-5 mL of toluene over 1 h at 0 °C. After the reaction time indicated in Table 1, the reaction mixture was concentrated in vacuo, and 5 mL each of water and pentane were added. Extractive workup provided essentially pure cyanohydrin TMS ether from which cyanohydrin was obtained by stirring with 5 mL of 2 N HCl and 5 mL of EtOAc, isolation from the EtOAc layer, and passage through a column of silica gel.