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. 2011 Dec 28;133(51):20738-41.
doi: 10.1021/ja210025q. Epub 2011 Dec 5.

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

Tomotsugu Awano  1 , Toshimichi Ohmura, Michinori Suginome
Affiliations

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

Tomotsugu Awano et al. J Am Chem Soc. .

Abstract

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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