Palladium-Catalyzed Cross-Coupling Reaction of Triorganoindium Reagents with Propargylic Esters

Citations Over TimeTop 10% of 2006 papers

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.

Related Papers

• → Enantiomeric enrichment of non-racemic mixtures of binaphthol with non-chiral packings(1996)47 cited
• → Enantiomeric enrichment by the use of density differences between racemic compounds and optically active enantiomers(1995)16 cited
• → Colour indicator for enantiomeric excess and assignment of the configuration of the major enantiomer of an amino acid ester(2002)26 cited
• → A method for determining the enantiomeric purity of profens(2009)14 cited
• → Photoinduced regioselective arylation of N-vinyllactams and methylthiazoles by tetrachlorophthalimides(2013)1 cited