Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl <i>meso</i>-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts
作者:Yuki Hashimoto、Chiaki Michimuko、Koki Yamaguchi、Makoto Nakajima、Masaharu Sugiura
DOI:10.1021/acs.joc.9b00827
日期:2019.7.19
as a catalyst, 1,2-diols, 1,3-diols, and catechol were selectively monoacylated. Furthermore, the highly enantioselective desymmetrization of meso-tartrates was achieved for the first time, utilizing 2-pyridyl esters and NiBr2/AgOPiv/Ph-BOX in CH3CN or CuCl2/AgOPiv/Ph-BOX in EtOAc catalyst systems (up to 96% ee). The latter catalyst system was also effective for the kinetic resolution of dibenzyl dl-tartrate
用2-吡啶基苯甲酸酯作为酰化剂和Zn(OAc)2作为催化剂,1,2-二醇,1,3-二醇和邻苯二酚被选择性地单酰化。此外,首次实现了酒石酸内消旋酒石酸酯的高对映选择性去对称化,这是通过在CH 3 CN中使用2-吡啶基酯和NiBr 2 / AgOPiv / Ph-BOX或在EtOAc催化剂体系中使用CuCl 2 / AgOPiv / Ph-BOX来实现的(对等)到96%ee)。后者的催化剂体系,也是有效的苄动力学拆分DL -酒石酸盐。