Novel Lewis acid-assisted chiral Lewis acid (LLA) system: Development of boroxin-Ti-BINOL-catalyzed asymmetric allylation of aldehydes

Synlett

Volumn , Issue 13, 2004, Pages 2437-2439

  Xia, Guoyao ^a   Shibatomi, Kazutaka ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Aldehydes; Allylations; Asymmetric catalysis; Lewis acid assisted chiral Lewis acid catalysts; Titanium

Indexed keywords

ALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; FLUORINE DERIVATIVE; LEWIS ACID; TITANIUM;

ACIDITY; ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 8644256724     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832830     Document Type: Article

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43. 4 and BINOL (1:1) catalyze the allylation of benzaldehyde very slowly at -20 °C even in the presence of activated molecular sieves [10 mol% (Ti), 70 h, 88% yield, 95% ee]. See ref.7c
44. A referee has argued that an ionic complex made up of borane-isopropoxide ate complex and cationic titanium(IV) triisopropoxide could be formed and act as catalyst.
45. Maruoka has reported bis[binaphthoxy(isopropoxy)titanium] oxide having Ti-O-Ti bond. In this paper, they assumed this type activation system (LLA) as one of the possible intermediates for the reaction. See ref.7s. Another possibility in our system is that the monomer of aryl boroxin would coordinate to an oxygen atom on Ti-BINOL complex and enhance the Lewis acidity of titanium in the same fashion, which seem to be also an example of LLA activation.
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