Enantioselective Aerobic Oxidative C(sp3)-H Olefination of Amines via Cooperative Photoredox and Asymmetric Catalysis

被引：115

作者：

Wei, Guo ^{[1
]}

Zhang, Chenhao ^{[1
]}

Bures, Filip ^{[2
]}

Ye, Xinyi ^{[3
]}

Tan, Choon-Hong ^{[3
]}

Jiang, Zhiyong ^{[1
]}

机构：

[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China

[2] Univ Pardubice, Fac Chem Technol, Inst Organ Chem & Technol, Studentska 573, Pardubice 53210, Czech Republic

[3] Nanyang Technol Univ, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore

来源：

ACS CATALYSIS | 2016年 / 6卷 / 06期

关键词：

asymmetric cooperative catalysis; photoredox catalysis; organocatalysis; aerobic oxidative olefination; beta-carbolines; C-H BONDS; DUAL-CATALYSIS; CYCLIC IMINES; FUNCTIONALIZATION; ORGANOCATALYSIS; ACID; PHOTOCATALYSIS; HYDROGENATION; ALKYLATION; ACTIVATION;

D O I：

10.1021/acscatal.6b00846

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A cooperative photoredox and asymmetric catalysis for the enantioselective aerobic oxidative C(sp(3))-H olefination of tetrahydro-beta-carbolines (THCs) is reported. This method, which is also effective for tetrahydroisoquinolines (THIQs), features a triple-catalyst strategy, involving a dicyanopyrazine-derived chromophore (DPZ) as the metal-free photoredox catalyst, a chiral Lewis base catalyst, and an inorganic salt cocatalyst. The current protocol provides straightforward access to a series of valuable a-substituted THCs and THIQs in high yields with excellent regio- and enantioselectivities (up to 95% ee).

引用

页码：3708 / 3712

页数：5

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