Palladium-catalyzed cross-coupling reaction of triorganoindium reagents with propargylic esters.
[reaction: see text] Triorganoindium reagents (R(3)In) react with propargylic esters under palladium catalysis via an S(N)2' rearrangement to afford allenes in good yields and with high regioselectivity. The reaction proceeds smoothly at room temperature with a variety of R(3)In (aryl, alkenyl, alkynyl, and methyl). When chiral, nonracemic propargylic esters are employed, the reaction takes place with high anti-stereoselectivity providing allenes with high enantiomeric excess.
Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain.
Ricardo
R
Riveiros
David
D
Rodríguez
José
J
Pérez Sestelo
Luis A
LA
Sarandeses