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Synfacts 2010(9): 1072-1072
DOI: 10.1055/s-0030-1257964
DOI: 10.1055/s-0030-1257964
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
An Organocatalytic β-Boration of α,β-Unsaturated Carbonyl Compounds
A. Bonet, H. Gulyás*, E. Fernández*
Universitat Rovira I Virgili, Tarragona, Spain
Further Information
Publication History
Publication Date:
23 August 2010 (online)
Significance
The authors report a chiral phospine-1-catalyzed β-boration of α,β-unsaturated carbonyl compounds using (Bpin)2 as borylating agent. The products were obtained in high conversions and optical purities. The mechanistic rationale is based on the phosphine coordination to one of the boron atoms, inducing a high polarization and presumably partial dissociation of the B-B bond. Thus, the potentially more nucleophilic boron atom could as such add to the double bond of the substrate in a phosphine-mediated chiral environment. Alcoholysis of the intermediate can then liberate the product and the boronic acid ester byproduct.