Ate Complexes of Secondary Boronic Esters as Chiral Organometallic-Type Nucleophiles for Asymmetric Synthesis

作者：Larouche Gauthier Robin; Elford Tim G; Aggarwal Varinder K^*

来源：Journal of the American Chemical Society, 2011, 133(42): 16794-16797.

DOI：10.1021/ja2077813

The addition of an aryllithium reagent to a secondary boronic ester leads to an intermediate boron-ate complex that behaves as a chiral nucleophile, reacting with a broad range of electrophiles with inversion of stereochemistry. Depending on the electrophile, the C-B bond can be converted into C-I, C-Br, C-Cl, C-N, C-O, and C-C, all with very high levels of stereocontrol. This discovery now adds a new, readily available, configurationally stable, chiral organometallic-type reagent to the arsenal of methods for use in asymmetric organic synthesis.

• 出版日期2011-10-26