Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts
Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts
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DOI：
10.1021/acs.joc.9b00827
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发表时间：
2019-07-19
影响因子：
3.6
通讯作者：
Sugiura, Masaharu
中科院分区：
文献类型：
--
作者：
Hashimoto, Yuki;Michimuko, Chiaki;Sugiura, Masaharu
以2-吡啶基苯甲酸酯为酰化剂，Zn(OAc)(2)为催化剂，选择性单酰化1,2-二醇、1,3-二醇和儿茶酚。此外，利用 2-吡啶酯和 NiBr2/AgOPiv/Ph-BOX 在 CH3CN 中或 CuCl2/AgOPiv/Ph-BOX 在 EtOAc 催化剂体系中（高达 96% ee），首次实现了内消旋酒石酸盐的高度对映选择性去对称化。后一种催化剂体系对于DL-酒石酸二苄酯的动力学拆分也有效。
With 2-pyridyl benzoates as acylating agents and Zn(OAc)(2) 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.