Rhodium(III)-Catalyzed Atroposelective Synthesis of C-N Axially Chiral Naphthylamines and Variants via C-H Activation

被引：40

作者：

Wang, Peiyuan ^{[1
]}

Huang, Yaling ^{[1
]}

Jing, Jierui ^{[1
]}

Wang, Fen ^{[1
]}

Li, Xingwei ^{[1
]}

机构：

[1] Shaanxi Normal Univ SNNU, Sch Chem & Chem Engn, Xian 710062, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 13期

关键词：

CATALYTIC ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SULFOXONIUM YLIDES; ANILIDES; ATROPISOMERS; CONSTRUCTION; ALLYLATION; LIGANDS; BINOL; BINAP;

D O I：

10.1021/acs.orglett.2c00686

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein is the efficient and atroposelective construction of two categories of C-N atropisomers via rhodium(III)-catalyzed C-H activation of sulfoxonium ylides en route to [4+2] annulation with sterically hindered, electron-rich alkynes. This reaction proceeds with high regio- and enantioselectivity under redox-neutral conditions via a double-substrate activation strategy, providing a novel entry to C-N axially chiral 4-functionalized 1-naphthols.

引用

页码：2531 / 2535

页数：5

共 53 条

[1] Chirally aminated 2-naphthols-organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel-Crafts amination [J].

Brandes, S ;

Bella, M ;

Kjoersgaard, A ;

Jorgensen, KA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) :1147-1151

[2] Atroposelective synthesis of axially chiral biaryl compounds [J].

Bringmann, G ;

Mortimer, AJP ;

Keller, PA ;

Gresser, MJ ;

Garner, J ;

Breuning, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427

[3] Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products [J].

Bringmann, Gerhard ;

Gulder, Tanja ;

Gulder, Tobias A. M. ;

Breuning, Matthias .

CHEMICAL REVIEWS, 2011, 111 (02) :563-639

[4] Update 1 of: BINOL: A Versatile Chiral Reagent [J].

Brunel, Jean Michel .

CHEMICAL REVIEWS, 2007, 107 (09) :PR1-PR45

[5] Modified BINOL ligands in asymmetric catalysis [J].

Chen, Y ;

Yekta, S ;

Yudin, AK .

CHEMICAL REVIEWS, 2003, 103 (08) :3155-3211

[6] Recent Advances in Catalytic Asymmetric Construction of Atropisomers [J].

Cheng, Jun Kee ;

Xiang, Shao-Hua ;

Li, Shaoyu ;

Ye, Liu ;

Tan, Bin .

CHEMICAL REVIEWS, 2021, 121 (08) :4805-4902

[7] The Challenge of Atropisomerism in Drug Discovery [J].

Clayden, Jonathan ;

Moran, Wesley J. ;

Edwards, Paul J. ;

LaPlante, Steven R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (35) :6398-6401

[8] Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity [J].

Giri, Ramesh ;

Shi, Bing-Feng ;

Engle, Keary M. ;

Maugel, Nathan ;

Yu, Jin-Quan .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3242-3272

[9] Cp*Co(III)-Catalyzed oxidative [5+2] annulation: regioselective synthesis of 2-aminobenzoxepines via C-H/O-H functionalization of 2-vinylphenols with ynamides [J].

Han, Xiang-Lei ;

Liu, Xu-Ge ;

Lin, E. ;

Chen, Yunyun ;

Chen, Zhuangzhong ;

Wang, Honggen ;

Li, Qingjiang .

CHEMICAL COMMUNICATIONS, 2018, 54 (82) :11562-11565

[10] Synthesis of Naphthols by Rh(III)-Catalyzed Domino C-H Activation, Annulation, and Lactonization Using Sulfoxonium Ylide as a Traceless Directing Group [J].

Hanchate, Vinayak ;

Kumar, Anil ;

Prabhu, Kandikere Ramaiah .

ORGANIC LETTERS, 2019, 21 (20) :8424-8428

← 1 2 3 4 5 6 →