title: Inversion or retention? Effects of acidic additives on the stereochemical course in enantiospecific Suzuki-Miyaura coupling of α-(acetylamino)benzylboronic esters.
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.
authors: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.
authors: Tomotsugu
authors: T
authors: Awano
authors: Toshimichi
authors: T
authors: Ohmura
authors: Michinori
authors: M
authors: Suginome