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Regio- and stereocontrolled access to γ-boronated unsaturated amino esters and derivatives from (Z)-alkenyl 1,2-bis(boronates). 2014

Tailor Sridhar, and Fabienne Berrée, and Gangavaram V M Sharma, and Bertrand Carboni
Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 , 263 Avenue du Général Leclerc, Campus de Beaulieu, Bâtiment 10A, 35042 Rennes Cedex, France.

The Borono-Mannich reaction of (Z)-1-alkene-1,2-diboronic esters proceeded regioselectively at the terminal C-B bond to afford (E)-γ-boronated unsaturated amino esters in good yields. These compounds were then subjected to Suzuki couplings for the creation of diversely substituted olefinic amino acid systems. Several other functional transformations were also carried out to illustrate the synthetic utility of the Petasis products.

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