Subscribe to RSS
DOI: 10.1055/s-0030-1259342
Enantioconvergent Synthesis of Allyl Boronates
H. Ito*, S. Kunii, M. Sawamura
Hokkaido University, Sapporo and PRESTO, Japan Science and Technology Agency, Saitama, Japan
Publication History
Publication Date:
19 January 2011 (online)

Significance
The authors report a remarkable copper-catalyzed enantioconvergent borylation reaction of cyclic allylic ethers, in which each enantiomer of the racemic mixture is converted into the same enantiomer of the product through different reaction pathways. This is a rare phenomenon and in contrast to dynamic kinetic resolutions (DKR) and dynamic kinetic asymmetric transformations (DYKAT), there is no equilibration of enantiomers or loss of chirality. The allyl boronates are extremely versatile reagents for organic synthesis, and the authors demonstrate the utility of these reagents for the stereoselective construction of quaternary centers.