Enantioselective nickel-catalyzed electrochemical reductive conjugate alkenylation of α,β-unsaturated ketones

被引：1

作者：

Somprasong, Siriphong ^{[1
]}

Wan, Bin ^{[1
]}

Harutyunyan, Syuzanna R. ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, Nijenborgh 3, NL-9747 AG Groningen, Netherlands

来源：

CHEMICAL SCIENCE | 2025年 / 16卷 / 02期

基金：

欧洲研究理事会;

关键词：

ASYMMETRIC 1,4-ADDITION; ORGANONICKEL COMPLEXES; ALKENYLBORONIC ACIDS; ARYL; ADDITIONS; ALKENES; ALPHA; REAGENTS; ELECTROLYSIS; ALKYLATION;

D O I：

10.1039/d4sc06891b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic electrochemical asymmetric catalysis is emerging as a promising strategy for the synthesis of chiral compounds. Herein, we report an asymmetric electrochemical nickel-catalysed reductive conjugate addition of alkenyl bromides/aryl iodides to alpha,beta-unsaturated ketones in an undivided cell, leading to addition products with high yields and excellent enantioselectivities (up to 96% yield and 96% ee).

引用

页码：802 / 808

页数：7

共 94 条

[1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823

[2]

Alexakis A, 2014, COPPER-CATALYZED ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/9783527664573

[3] A synthesis of (-)-mintlactone [J].

Bates, Roderick W. ;

Sridhar, S. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) :8104-8105

[4] Retooling Asymmetric Conjugate Additions for Sterically Demanding Substrates with an Iterative Data-Driven Approach [J].

Brethome, Alexandre V. ;

Paton, Robert S. ;

Fletcher, Stephen P. .

ACS CATALYSIS, 2019, 9 (08) :7179-7187

[5] Enantioselective total synthesis of clavirolide C. applications of Cu-catalyzed asymmetric conjugate additions and Ru-catalyzed ring-closing metathesis [J].

Brown, M. Kevin ;

Hoveyda, Amir H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) :12904-+

[6] Highly reactive σ-organonickel complexes in electrocatalytic processes [J].

Budnikova, YH ;

Perichon, J ;

Yakhvarov, DG ;

Kargin, YM ;

Sinyashin, OG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 630 (02) :185-192

[7] Dehydrogenative reagent-free annulation of alkenes with diols for the synthesis of saturated O-heterocycles [J].

Cai, Chen-Yan ;

Xu, Hai-Chao .

NATURE COMMUNICATIONS, 2018, 9

[8]

Cendrineau T., 2009, Org. Lett., V11, P3486

[9]

Chang X., 2020, Angew. Chem., Int. Ed., V132, P12712, DOI [10.1002/ange.202000016, DOI 10.1002/ANGE.202000016]

[10] Merging Electrosynthesis and Bifunctional Squaramide Catalysis in the Asymmetric Detrifluoroacetylative Alkylation Reactions [J].

Chang, Xihao ;

Zhang, Jiayin ;

Zhang, Qinglin ;

Guo, Chang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (42) :18500-18504

← 1 2 3 4 5 6 7 8 9 10 →