通过联合交叉偶联反应对碳环和杂环叔硼酸酯进行对映选择性构建
Enantioselective Construction of Carbocyclic and Heterocyclic Tertiary Boronic Esters by Conjunctive Cross-Coupling Reaction.
作者信息
Zhang Xuntong, Gao Chenpeng, Morken James P
机构信息
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
出版信息
J Am Chem Soc. 2023 Aug 2;145(30):16344-16349. doi: 10.1021/jacs.3c05815. Epub 2023 Jul 24.
Abstract
Synthesis of stereodefined carbocyclic and heterocyclic tertiary boronic esters is accomplished by performing a conjunctive cross-coupling reaction on preformed cyclic boron ate complexes. Boronates bearing spirocyclic and aryl bicyclic skeletons can be synthesized enantioselectively using a chiral PHOX-ligated Pd catalyst with achiral starting material, while substrates bearing continuous stereogenic centers can be generated diastereoselectively. A variety of aryl and alkenyl electrophiles are incorporated.
摘要
通过对预先形成的环状硼酸酯络合物进行联合交叉偶联反应，可实现立体定向碳环和杂环叔硼酸酯的合成。带有螺环和芳基双环骨架的硼酸酯可以使用手性PHOX配体的钯催化剂与非手性起始原料进行对映选择性合成，而带有连续立体中心的底物可以进行非对映选择性生成。引入了多种芳基和烯基亲电试剂。
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