Mechanistic insights into the catalytic asymmetric allylboration of ketones: Bronsted or Lewis acid activation?

Journal article

Binaphthol ligands promote the enantioselective addition of allylboronates to ketones. In this study, we use DFT calculations to establish the identity of the reacting chiral species. Our results show that a cyclic Lewis acid-activated boronate is the most reactive species on the basis of calculated energy barriers, and it is only this species that leads to the correct enantiomer. The stereoinduction can be rationalized in terms of the competing chairlike transition structures.

Authors: Paton, R; Goodman, J; Pellegrinet, S

• Publication status: Published
• Journal: Organic letters
• Volume: 11
• Issue: 1
• Pages: 37-40
• Publication date: 2009-01-01
• DOI: 10.1021/ol802270u
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English
• Keywords: Catalysis; Stereoisomerism; Ketones; Boronic Acids; Naphthols; Molecular Structure; Models, Chemical; Ligands; Allyl Compounds; Boranes