One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines

被引：11
|
作者：
Sangster, Jack J. [1 ]
Ruscoe, Rebecca E. [1 ]
Cosgrove, Sebastian C. [1 ,2 ]
Mangas-Sanchez, Juan [1 ,3 ]
Turner, Nicholas J. [1 ]
机构：
[1] Univ Manchester, Manchester Inst Biotechnol, Dept Chem, Manchester M1 7DN, Lancs, England
[2] Keele Univ, Sch Chem & Phys Sci, Lennard Jones Lab, Keele ST5 5BG, Staffs, England
[3] Aragonese Fdn Res & Dev ARAID, Inst Chem Synth & Homogeneous Catalysis ISQCH CSI, Pedro Cerbuna 12, Zaragoza 50009, Spain
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2023年 / 145卷 / 08期
基金：
英国生物技术与生命科学研究理事会;
关键词：
OXIDASE MAO-N; MONOAMINE-OXIDASE; ASYMMETRIC-SYNTHESIS; AMINE OXIDASE; CATALYZED DERACEMIZATION; CARBONYL-COMPOUNDS; H BONDS; ALLYLATION; IMINES; DERACEMISATION;
D O I：
10.1021/jacs.2c09176
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, we report a one-pot, chemoenzymatic process for the synthesis of enantioenriched C(1)-allylated tetrahydroisoquinolines. This transformation couples a monoamine oxidase (MAO-N)-catalyzed oxidation with a metal catalyzed allylboration, followed by a biocatalytic deracemization to afford allylic amine derivatives in both high yields and good to high enantiomeric excess. The cascade is operationally simple, with all components added at the start of the reaction and can be used to generate key building blocks for further elaboration.
引用
收藏
页码：4431 / 4437
页数：7
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