Highly diastereoselective palladium-catalyzed indium-mediated allylation of chiral hydrazones.

Org Lett

Department of Chemistry and Biochemistry, North Dakota State University, P.O. Box 6050, Fargo, North Dakota 58108-6050, United States.

Published: January 2015

The general and efficient palladium-catalyzed indium-mediated allylation of chiral hydrazones was accomplished with excellent yield (72-92%) and diastereoselectivity (up to 99:1). The development of this reaction and the substrate scope are described. The conversion was found to be proportional to the phosphine concentration, which provided insight into the mechanism and competing pathways of the redox transmetalation process.

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http://dx.doi.org/10.1021/ol5034207DOI Listing

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