Photoinduced synthesis of trisubstituted allylic molecules via migratory allylation of olefins

被引:0
作者
Xia, Dingding [1 ,2 ]
Zhang, Na [3 ]
Zhong, Mingdong [4 ]
Wang, Weijie [1 ]
Li, Qiannan [1 ,2 ]
Zhang, Yu [1 ,2 ]
Zhang, Wei-Dong [1 ,2 ,5 ]
机构
[1] Shanghai Univ Tradit Chinese Med, Inst Interdisciplinary Integrat Med Res, Shanghai Frontiers Sci Ctr Chinese Med Chem Biol, 1200 Cailun Rd, Shanghai 201203, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, State Key Lab Antiviral Drugs, Pingyuan Lab,NMPA Key Lab Res & Evaluat Innovat Dr, Xinxiang 453007, Henan, Peoples R China
[3] Tongji Univ, Sch Med, Shanghai East Hosp, Dept Lab Med, Shanghai 200120, Peoples R China
[4] Tianjin Normal Univ, Coll Chem, Tianjin Key Lab Struct & Performance Funct Mol, Tianjin 300387, Peoples R China
[5] Second Mil Med Univ, Sch Pharm, Shanghai 200433, Peoples R China
基金
中国国家自然科学基金;
关键词
ASYMMETRIC-SYNTHESIS; ALKYLATIONS; ARYLATION; ALDEHYDES; TERTIARY; ACIDS;
D O I
10.1039/d4cc05368k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A transition-metal-free method to afford diverse trisubstituted allylic molecules via migratory allylation of olefins under light irradiation is described. This system tolerated diverse N-tosylhydrazones and olefinic boronic acids. Successful allylation of drugs and natural-product analogues was achieved. The gram-scale synthesis and subsequent post-transformation demonstrated the potential applications of this strategy.
引用
收藏
页码:1653 / 1656
页数:4
相关论文
共 38 条
[1]  
Barluenga J, 2009, NAT CHEM, V1, P494, DOI [10.1038/NCHEM.328, 10.1038/nchem.328]
[2]   Photocatalytic Barbier reaction - visible-light induced allylation and benzylation of aldehydes and ketones [J].
Berger, Anna Lucia ;
Donabauer, Karsten ;
Koenig, Burkhard .
CHEMICAL SCIENCE, 2018, 9 (36) :7230-7235
[3]   ASYMMETRIC-SYNTHESIS OF THE DIASTEREOMERIC 1-(2-CYCLOHEXENYL)-1-ALKANOLS IN HIGH OPTICAL PURITY VIA A STEREOCHEMICALLY STABLE ALLYLIC BORANE, B-2-CYCLOHEXEN-1-YLDIISOPINOCAMPHEYLBORANE [J].
BROWN, HC ;
JADHAV, PK ;
BHAT, KS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2564-2565
[4]   Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates [J].
Butt, Nicholas A. ;
Zhang, Wanbin .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) :7929-7967
[5]   Olefination of Carbonyl Compounds through Reductive Coupling of Alkenylboronic Acids and Tosylhydrazones [J].
Carmen Perez-Aguilar, M. ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) :5953-5957
[6]   Transition Metal-Catalyzed Migratory Tsuji-Trost Reaction [J].
Chen, Xian-Xiao ;
He, Zhi-Tao .
CHEMCATCHEM, 2023, 15 (22)
[7]   Fluorescent Flippers: Small-Molecule Probes to Image Membrane Tension in Living Systems [J].
Chen, Xiao-Xiao ;
Bayard, Felix ;
Gonzalez-Sanchis, Nerea ;
Pamungkas, Khurnia Krisna Puji ;
Sakai, Naomi ;
Matile, Stefan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (20)
[8]   Palladium-catalyzed regio- and enantioselective migratory allylic C(sp3)-H functionalization [J].
Chen, Ye-Wei ;
Liu, Yang ;
Lu, Han-Yu ;
Lin, Guo-Qiang ;
He, Zhi-Tao .
NATURE COMMUNICATIONS, 2021, 12 (01)
[9]   Regio- and enantiospecific rhodium-catalyzed arylation of unsymmetrical fluorinated acyclic allylic carbonates: inversion of absolute configuration [J].
Evans, PA ;
Uraguchi, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (24) :7158-7159
[10]   Asymmetric synthesis of α-substituted allyl boranes and their application in the synthesis of iso-agatharesinol [J].
Fang, Guang Yu ;
Aggarwal, Varinder K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (03) :359-362