Iridium Catalysed Asymmetric Allylic Substitution Reaction of Indolizine Derivatives

被引:16
作者
Lu, Jiamin [1 ]
Wang, Meifang [1 ]
Xu, Ruigang [1 ]
Sun, Haizhou [1 ]
Zheng, Xuan [1 ]
Zhong, Guofu [1 ]
Zeng, Xiaofei [1 ]
机构
[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, 2318 Yuhangtang Rd, Hangzhou 311121, Peoples R China
基金
中国国家自然科学基金;
关键词
Iridium catalysis; Indolizine; Allylic substitution; Asymmetric synthesis; C3; FUNCTIONALIZATION; N-ALLYLATION; CONSTRUCTION; ARYLATION; ALCOHOLS; NITROGEN; OXYGEN;
D O I
10.1002/ajoc.202100171
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient direct asymmetric allylic substitution (AAS) reaction of indolizine derivatives with allylic alcohols for accessing enantioenriched indolizine derivatives was realized by combining a chiral iridium complex catalyst with Lewis acid under mild reaction conditions, delivering various chiral allylation products in remarkably high yields and excellent enantioselectivities. This protocol distinguishes itself by availability of the starting materials, mild reaction conditions, broad substrate scope, high yields, excellent selectivity and easy scale-up in a stereoselective manner, which provides a highly efficient protocol for chiral indolizines.
引用
收藏
页码:1500 / 1507
页数:8
相关论文
共 67 条
[41]   Palladium-Catalyzed Allylic Substitution Reaction of Benzothiazolylacetamide with Allylic Alcohols in Water [J].
Pan, Shulei ;
Wu, Binqiang ;
Hu, Jinjin ;
Xu, Ruigang ;
Jiang, Min ;
Zeng, Xiaofei ;
Zhong, Guofu .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (16) :10111-10119
[42]   Palladium-catalyzed arylation and heteroarylation of indolizines [J].
Park, CH ;
Ryabova, V ;
Seregin, IV ;
Sromek, AW ;
Gevorgyan, V .
ORGANIC LETTERS, 2004, 6 (07) :1159-1162
[43]   Applications of Iridium-Catalyzed Asymmetric Allylic Substitution Reactions in Target-Oriented Synthesis [J].
Qu, Jianping ;
Helmchen, Guenter .
ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (10) :2539-2555
[44]   Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation [J].
Rossi-Ashton, James A. ;
Clarke, Aimee K. ;
Donald, James R. ;
Zheng, Chao ;
Taylor, Richard J. K. ;
Unsworth, William P. ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (19) :7598-7604
[45]   Direct palladium-catalyzed alkynylation of N-fused heterocycles [J].
Seregin, Ilya V. ;
Ryabova, Victoria ;
Gevorgyan, Vladimir .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7742-+
[46]   Indolizine: a biologically active moiety [J].
Sharma, Vikas ;
Kumar, Vipin .
MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (08) :3593-3606
[47]   Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Bronsted Acid Catalysis [J].
Shen, Dan ;
Chen, Qiliang ;
Yan, Peipei ;
Zeng, Xiaofei ;
Zhong, Guofu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) :3242-3246
[48]   Catalyst-Free Conjugate Addition of Indolizines to In Situ-Generated Oxidized Morita-Baylis-Hillman Adducts [J].
Silva, Thiago S. ;
Zeoly, Lucas A. ;
Coelho, Fernando .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08) :5438-5448
[49]   Recent progress in synthesis and bioactivity studies of indolizines [J].
Singh, Girija S. ;
Mmatli, Edward E. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) :5237-5257
[50]   An In silico Approach for Identification of Novel Inhibitors as a Potential Therapeutics Targeting HIV-1 Viral Infectivity Factor [J].
Sinha, Chanda ;
Nischal, Anuradha ;
Bandaru, Srinivas ;
Kasera, Priyadarshani ;
Rajput, Ashish ;
Nayarisseri, Anuraj ;
Khattri, Sanjay .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2015, 15 (01) :65-72