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  • Catalytic asymmetric synthesis with rh-diene complexes: 1,4-addition of arylboronic acids to unsaturated esters.

Catalytic asymmetric synthesis with rh-diene complexes: 1,4-addition of arylboronic acids to unsaturated esters.

Organic letters (2005-08-12)
Jean-François Paquin, Corey R J Stephenson, Christian Defieber, Erick M Carreira
ABSTRACT

A general route to enantioenriched tert-butyl 3,3-diarylpropanoates is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to unsaturated tert-butyl esters in the presence of chiral dienes as ligands. The addition of both electron-poor and electron-rich boronic acids proceeds smoothly with various enoates in 63-90% yield with high enantioselectivites (89-94% ee). [reaction: see text]