Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration

被引:25
作者
Groves, Alistair [1 ,2 ]
Sun, Jinwei [1 ,2 ,3 ]
Parke, Hal R. I. [1 ,2 ]
Callingham, Michael [1 ,2 ]
Argent, Stephen P. [2 ]
Taylor, Laurence J. [2 ]
Lam, Hon Wai [1 ,2 ]
机构
[1] Univ Nottingham, GlaxoSmithKline Carbon Neutral Labs Sustainable C, Jubilee Campus,Triumph Rd, Nottingham NG7 2TU, England
[2] Univ Nottingham, Sch Chem, Univ Pk, Nottingham NG7 2RD, England
[3] Nanjing Univ Informat Sci & Technol, Jiangsu Collaborat Innovat Ctr Atmospher Environm, Jiangsu Key Lab Atmospher Environm Monitoring & P, Sch Chem & Mat Sci, Nanjing 210044, Jiangsu, Peoples R China
基金
英国工程与自然科学研究理事会;
关键词
REMOTE FUNCTIONALIZATION; C-C; ARYLBORONIC ACIDS; RHODIUM; ISOMERIZATION; ALLYLATION; 1,3-ENYNES; COMPLEXES; EFFICIENT; REAGENTS;
D O I
10.1039/c9sc06309a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective synthesis of densely functionalized polycarbocycles by the rhodium(i)-catalyzed reaction of arylboronic acids with 1,3-diketones is described. The key step in these desymmetrizing domino addition-cyclization reactions is an alkenyl-to-aryl 1,4-Rh(i) migration, which enables arylboronic acids to function effectively as 1,2-dimetalloarene surrogates.
引用
收藏
页码:2759 / 2764
页数:6
相关论文
共 44 条
[21]   Ketone synthesis by intramolecular acylation of organorhodium(I) with ester [J].
Miura, T ;
Sasaki, T ;
Nakazawa, H ;
Murakami, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (05) :1390-1391
[22]   Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(i) migration [J].
O'Brien, Luke ;
Karad, Somnath Narayan ;
Lewis, William ;
Lam, Hon Wai .
CHEMICAL COMMUNICATIONS, 2019, 55 (76) :11366-11369
[23]   Merry-go-round multiple alkylation on aromatic rings via rhodium catalysis [J].
Oguma, K ;
Miura, M ;
Satoh, T ;
Nomura, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) :10464-10465
[24]   Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration [J].
Partridge, Benjamin M. ;
Callingham, Michael ;
Lewis, William ;
Lam, Hon Wai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) :7227-7232
[25]   Iridium-Catalyzed Arylative Cyclization of Alkynones by 1,4-Iridium Migration [J].
Partridge, Benjamin M. ;
Gonzalez, Jorge Solana ;
Lam, Hon Wai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) :6523-6527
[26]   Transition metal-catalyzed direct remote C-H functionalization of alkyl groups via C(sp3)-H bond activation [J].
Qiu, Guanyinsheng ;
Wu, Jie .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (02) :169-178
[27]   Iridium-catalyzed 1,5-(aryl)aminomethylation of 1,3-enynes by alkenyl-to-allyl 1,4-iridium(i) migration [J].
Ruscoe, Rebecca E. ;
Callingham, Michael ;
Baker, Joshua A. ;
Korkis, Stamatis E. ;
Lam, Hon Wai .
CHEMICAL COMMUNICATIONS, 2019, 55 (06) :838-841
[28]   Rhodium/diene-catalyzed tandem 1,4-shift/1,4-addition of (E)-1,2-diphenylethenylboronic acid to enones: density functional theory modeling and asymmetric catalysis [J].
Sasaki, Keigo ;
Nishimura, Takahiro ;
Shintani, Ryo ;
Kantchev, Eric Assen B. ;
Hayashi, Tamio .
CHEMICAL SCIENCE, 2012, 3 (04) :1278-1283
[30]   Enantioenriched 1-Tetralones via Rhodium-Catalyzed Arylative Cascade Desymmetrization/Acylation of Alkynylmalonates [J].
Selmani, Aymane ;
Darses, Sylvain .
ORGANIC LETTERS, 2019, 21 (19) :8122-8126