Palladium-catalyzed cross-coupling reaction of triorganoindium reagents with propargylic esters.

Riveiros, R.; Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A.


Org. Lett. 2006, 8, 1403–1406 (DOI: 10.1021/ol060192o).

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Triorganoindium reagents (R3In) react with propargylic esters under palladium catalysis via an SN2’ rearrangement to afford allenes in good yields and with high regioselectivity. The reaction proceeds smoothly at room temperature with a variety of R3In (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.