Palladium-Catalyzed Cross-Coupling Reaction of Triorganoindium Reagents with Propargylic Esters
- 1 March 2006
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (7) , 1403-1406
- https://doi.org/10.1021/ol060192o
Abstract
[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.Keywords
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