Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes
作者:Jian Chen、Shaolin Zhu
DOI:10.1021/jacs.1c07851
日期:2021.9.8
functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It useschiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization
已经开发出一种镍催化、多组分区域选择性和对映选择性偶联,通过顺序加氢甲酰化和羰基化从容易获得的起始材料中进行。这种模块化的多组分加氢官能化策略能够对各种未活化的烯烃进行直接的还原烃基化,以产生各种带有功能化 α-立体中心的不对称二烷基酮,包括对映体富集的手性 α-芳基酮和 α-氨基酮。它使用手性双恶唑啉作为配体,硅烷作为还原剂,氯甲酸酯作为安全的 CO 源,外消旋仲苄基氯或N受保护的 α-氨基酸的 -羟基邻苯二甲酰亚胺 (NHP) 酯作为烷基化试剂。该过程的良性性质使该方法适用于复杂分子的后期功能化。
A novel copper (i) mediated, symmetrical coupling procedure for alkyl, aryl, benzyl, and thiophenyl dihalides
作者:David K. Johnson、Jeffrey P Ciavarri、Faoud T Ishmael、Kurl J. Schillinger、Thomas A.P. van Geel、Stephen M. Stratton
DOI:10.1016/0040-4039(95)01850-h
日期:1995.11
were obtained with Li2CuCl3 and the following trends in halide reactivity were observed Br > Cl for alkyl, aryl, and thiophenyl dihalides. and benzyl halide > phenyl halide. Utilizing these trends, a symmetrical coupling procedure for alkyl. aryl benzyl and thiophenyl dihalides, simply carried out by combining the dihalide with metallic magnesium and Li2CuCl4 is reported
Copper-Catalyzed Enantioselective Markovnikov Protoboration of α-Olefins Enabled by a Buttressed N-Heterocyclic Carbene Ligand
作者:Yuan Cai、Xin-Tuo Yang、Shuo-Qing Zhang、Feng Li、Yu-Qing Li、Lin-Xin Ruan、Xin Hong、Shi-Liang Shi
DOI:10.1002/anie.201711229
日期:2018.1.26
Reported is a highly enantioselective copper‐catalyzed Markovnikov protoboration of unactivatedterminalalkenes. A variety of simple and abundant feedstock α‐olefins bearing a diverse array of functional groups and heterocyclic substituents can be used as substrates, and the reaction proceeds under mild reaction conditions at ambient temperature to provide expedient access to enantioenriched alkylboronic