Diarylborinic acid derivatives as a catalytic iminium ion generator in the mannich-type reaction using secondary amines, aldehydes, and ketene silyl acetals

Synlett

Volumn , Issue 8, 2008, Pages 1239-1242

  Tanaka, Yusuke ^a   Hasui, Tomoaki ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

amino acids; Boron based catalyst; Iminium ion intermediate; Ketene silyl acetal; Nucleophilic additions

Indexed keywords

ACETAL DERIVATIVE; ALDEHYDE; AMINE; BORINIC ACID DERIVATIVE; ESTER; ION; KETENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; MANNICH REACTION;

EID: 44349190183     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072724     Document Type: Article

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32. 4 and evaporated under vacuum. The crude 5 was purified by silica gel column chromatography. The imine-containing products 8 and 10 could not be purified by column chromatography, but were isolated by bulb-to-bulb distillation.
33. The imine-amine conjugate 7 exists as the cyclized aminal form, which may be in equilibrium with the imine form shown in the scheme.