反转还是保留？酸性添加剂对 α-（乙酰氨基）苄基硼酸酯的对映选择性 Suzuki-Miyaura 偶联反应立体化学过程的影响。
Inversion or retention? Effects of acidic additives on the stereochemical course in enantiospecific Suzuki-Miyaura coupling of α-(acetylamino)benzylboronic esters.
机构信息
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.
出版信息
J Am Chem Soc. 2011 Dec 28;133(51):20738-41. doi: 10.1021/ja210025q. Epub 2011 Dec 5.
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.
在 Pd/XPhos 催化剂体系存在下，通过选择酸性添加剂，可以改变手性α-（乙酰氨基）苄基硼酸酯与芳基溴化物的立体特异性 Suzuki-Miyaura 偶联的立体化学过程。使用苯酚作为添加剂时，会发生高度对映选择性的反转 C-C 键形成。相比之下，当使用 Zr(Oi-Pr)(4)·i-PrOH 作为添加剂时，则可以获得对构型保持的高对映选择性。
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