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Inversion or retention? Effects of acidic additives on the stereochemical course in enantiospecific Suzuki-Miyaura coupling of α-(acetylamino)benzylboronic esters. | LitMetric
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Inversion or retention? Effects of acidic additives on the stereochemical course in enantiospecific Suzuki-Miyaura coupling of α-(acetylamino)benzylboronic esters.

Tomotsugu Awano Toshimichi Ohmura Michinori Suginome

J Am Chem Soc

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.

Published: December 2011

The stereochemical course of the stereospecific Suzuki-Miyaura coupling of enantioenriched α-(acetylamino)benzylboronic esters with aryl bromides can be switched by the choice of acidic additives in the presence of a Pd/XPhos catalyst system. Highly enantiospecific, invertive C-C bond formation takes place with the use of phenol as an additive. In contrast, high enantiospecificity for retention of configuration is attained in the presence of Zr(Oi-Pr)(4)·i-PrOH as an additive.

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http://dx.doi.org/10.1021/ja210025qDOI Listing

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