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DOI: 10.1055/s-0030-1258672
Allylboration of Aldehydes
Contributor(s):Benjamin List, Saihu LiaoUniversity of South Florida, Tampa, USA
Chiral Brønsted Acid Catalyzed Allylboration of Aldehydes
J. Am. Chem. Soc. 2010, 132: 11884-11886
Publication History
Publication Date:
22 September 2010 (online)
Key words
allylboration - aldehydes - TRIP
Significance
A highly enantioselective allylboration of aldehydes catalyzed by the chiral Brønsted acid (R)-TRIP is reported by the authors. This transformation shows a broad substrate scope: aryl, heteroayrl, α,β-unsaturated and aliphatic aldehydes can all be efficiently allylated. Furthermore, the crotylboration of benzaldehyde also proceeded smoothly with high diastereo- and enantioselectivity in the presence of this acid catalyst.
Comment
Simple starting materials and a commercially available catalyst make this protocol a useful and efficient method for the synthesis of enantioenriched homoallylic alcohols. A transition state where the boronate is activated by protonation of the boronate oxygen with a chiral phosphoric acid is proposed by the authors. To confirm this activation model, further mechanistic investigation may be required.