Palladium-Catalyzed Four-Component Cascade Reaction for the Synthesis of Highly Functionalized Acyclic O,O-Acetals

被引：18
作者：
Xiong, Wenfang [1 ]
Yan, Donghao [1 ]
Qi, Chaorong [1 ]
Jiang, Huanfeng [1 ]
机构：
[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 03期
基金：
中国国家自然科学基金;
关键词：
C-H BONDS; CARBON-DIOXIDE; PROPARGYLIC ALCOHOLS; ASYMMETRIC ADDITION; EFFICIENT SYNTHESIS; CO2; INCORPORATION; ATMOSPHERIC CO2; MULTICOMPONENT REACTIONS; N-TOSYLHYDRAZONES; METAL-FREE;
D O I：
10.1021/acs.orglett.7b03808
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed four-component cascade reaction of carbon dioxide, amines, allenyl ethers, and aryl iodides has been developed for the first time. The novel reaction allows simultaneous construction of three different new bonds (C-N, C-O, and C-C) in a single step, affording an efficient method for the synthesis of a variety of highly functionalized acyclic O,O-acetals. Excellent chemo- and regioselectivity, wide substrate scope, and good functional group tolerance are features of the method.
引用
收藏
页码：672 / 675
页数：4
相关论文
共 82 条
[1]   Nonanomerlc spiroketals in natural products: Structures, sources, and synthetic strategies [J].
Aho, JE ;
Pihko, PM ;
Rissa, TK .
CHEMICAL REVIEWS, 2005, 105 (12) :4406-4440
[2]   Palladium-catalysed sequential carboxylation-alkoxycarbonylation of acetylenic amines [J].
Bacchi, A ;
Chiusoli, GP ;
Costa, M ;
Gabriele, B ;
Righi, C ;
Salerno, G .
CHEMICAL COMMUNICATIONS, 1997, (13) :1209-1210
[3]   Catalytic asymmetric addition of carbon dioxide to propylene oxide with unprecedented enantioselectivity [J].
Berkessel, Albrecht ;
Brandenburg, Marc .
ORGANIC LETTERS, 2006, 8 (20) :4401-4404
[4]   Synthesis of Lithium Boracarbonate Ion Pairs by Copper-Catalyzed Multi-Component Coupling of Carbon Dioxide, Diboron, and Aldehydes [J].
Carry, Beatrice ;
Zhang, Liang ;
Nishiura, Masayoshi ;
Hou, Zhaomin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (21) :6257-6260
[5]   Perspectives on the synthesis of organic carbamates [J].
Chaturvedi, Devdutt .
TETRAHEDRON, 2012, 68 (01) :15-45
[6]   A Novel Synthesis of 1,3-Oxazine-2,4-diones via a Simple and Efficient Reaction of CO2 with 2,3-Allenamides [J].
Chen, Guofei ;
Fu, Chunling ;
Ma, Shengming .
ORGANIC LETTERS, 2009, 11 (13) :2900-2903
[7]   Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? [J].
Cokoja, Mirza ;
Bruckmeier, Christian ;
Rieger, Bernhard ;
Herrmann, Wolfgang A. ;
Kuehn, Fritz E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8510-8537
[8]   Carbon Dioxide Capture: Prospects for New Materials [J].
D'Alessandro, Deanna M. ;
Smit, Berend ;
Long, Jeffrey R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (35) :6058-6082
[9]   Unified Total Syntheses of (-)-Medicarpin, (-)-Sophoracarpan A, and (±)-Kushecarpin A with Some Structural Revisions [J].
Feng, Zhen-Gao ;
Bai, Wen-Ju ;
Pettus, Thomas R. R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (06) :1864-1867
[10]   Strategies for Innovation in Multicomponent Reaction Design [J].
Ganem, Bruce .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (03) :463-472
123456789