Chiral Aryliodine-Catalyzed Asymmetric Oxidative C-N Bond Formation via Desymmetrization Strategy

被引:36
作者
Ding, Qiang [1 ,2 ]
He, Huan [1 ,2 ,3 ]
Cai, Qian [1 ,2 ]
机构
[1] Jinan Univ, Coll Pharm, 601 Huangpu Ave West, Guangzhou 510632, Guangdong, Peoples R China
[2] Hebei Univ Sci & Technol, Guangzhou City Key Lab Precis Chem Drug Dev, Shijiazhuang 050018, Hebei, Peoples R China
[3] Hebei Univ Sci & Technol, Coll Chem & Pharmaceut Engn, Shijiazhuang 050018, Hebei, Peoples R China
关键词
HYPERVALENT IODINE OXIDATION; ENANTIOSELECTIVE DESYMMETRIZATION; H AMINATION; DEAROMATIZATION; SPIROLACTONIZATION; REAGENTS; CYCLIZATION; CHEMISTRY; ARENES; ACID;
D O I
10.1021/acs.orglett.8b01849
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An asymmetric oxidative C-N bond-forming reaction is developed using a chiral diiodospirobiindane derivative as the catalyst and mCPBA as a terminal oxidant. The protocol is based on an asymmetric desymmetrization strategy and affords lactams or spirolactams according to the different substituents on the substrates. The products are obtained in good yields and moderate to high enantioselectivities.
引用
收藏
页码:4554 / 4557
页数:4
相关论文
共 57 条
[1]  
Akiba K-y., 1999, Chemistry of Hypervalent Compounds
[2]   Iodobenzene Catalyzed C-H Amination of N-Substituted Amidines Using m-Chloroperbenzoic Acid [J].
Alla, Santhosh Kumar ;
Kumar, Rapolu Kiran ;
Sadhu, Pradeep ;
Punniyamurthy, Tharmalingam .
ORGANIC LETTERS, 2013, 15 (06) :1334-1337
[3]   Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature [J].
Antonchick, Andrey P. ;
Samanta, Rajarshi ;
Kulikov, Katharina ;
Lategahn, Jonas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8605-8608
[4]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[5]   Stereoselective anhydride openings [J].
Atodiresei, Luliana ;
Schiffers, Ingo ;
Bolm, Carsten .
CHEMICAL REVIEWS, 2007, 107 (12) :5683-5712
[6]   OBSERVATIONS ON THE CHEMISTRY OF THE IODOXY GROUP [J].
BARTON, DHR ;
GODFREY, CRA ;
MORZYCKI, JW ;
MOTHERWELL, WB ;
STOBIE, A .
TETRAHEDRON LETTERS, 1982, 23 (09) :957-960
[7]  
de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V2nd
[8]   Organocatalyzed Enantioselective Desymmetrization of Diols in the Preparation of Chiral Building Blocks [J].
Diaz-de-Villegas, Maria D. ;
Galvez, Jose A. ;
Badorrey, Ramon ;
Lopez-Ram-de-Viu, M. Pilar .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (44) :13920-13935
[9]   Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant [J].
Dohi, T ;
Maruyama, A ;
Yoshimura, M ;
Morimoto, K ;
Tohma, H ;
Kita, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6193-6196
[10]   A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols [J].
Dohi, Toshifumi ;
Maruyama, Akinobu ;
Takenaga, Naoko ;
Senami, Kento ;
Minamitsuji, Yutaka ;
Fujioka, Hiromichi ;
Caemmerer, Simon B. ;
Kita, Yasuyuki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3787-3790