Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis

J Am Chem Soc. 2011 Oct 26;133(42):16794-7. doi: 10.1021/ja2077813. Epub 2011 Oct 4.

Abstract

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.