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

Tailor Sridhar (1) , Fabienne Berrée (2) , Gangavaram V M Sharma (1) , Bertrand Carboni (2)

1 Organic and Biomolecular Chemistry Division
2 ISCR - Institut des Sciences Chimiques de Rennes

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.

Keywords: Suzuki couplings; Petasis; Aminoesters; boronic esters

Domains: Chemical Sciences; Organic chemistry

Tailor Sridhar, Fabienne Berrée, Gangavaram V M Sharma, Bertrand Carboni. Regio- and stereocontrolled access to γ-boronated unsaturated amino esters and derivatives from (Z)-alkenyl 1,2-bis(boronates).. Journal of Organic Chemistry, 2014, 79 (2), pp.783-9. ⟨10.1021/jo402237t⟩. ⟨hal-00955530⟩