Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP

被引:20
作者
Zhang, Jie [1 ]
Shao, Ying [2 ]
Wang, Yaxiong [1 ]
Li, Huihuang [1 ]
Xu, Dongmei [1 ]
Wan, Xiaobing [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Changzhou Univ, Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
关键词
IODIDE-CATALYZED SYNTHESIS; OXIDATIVE AMINATION; COUPLING REACTIONS; CARBOXYLIC-ACIDS; TERTIARY-AMINES; BETA-KETOACIDS; ALLYLATION; AMIDATION; STRATEGY; BONDS;
D O I
10.1039/c5ob00109a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A transition-metal-free decarboxylation coupling process for the preparation of alpha-amino acid esters, which succeeded in merging hydrolysis/decarboxylation/nucleophilic substitution, is well described. This strategy uses commercially available inexpensive starting materials, catalysts and oxidants and has a wide substrate scope and operational simplicity.
引用
收藏
页码:3982 / 3987
页数:6
相关论文
共 55 条
[31]   Development of a decarboxylative palladation reaction and its use in a Heck-type olefination of arene carboxylates [J].
Myers, AG ;
Tanaka, D ;
Mannion, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11250-11251
[32]   Nonlinear Optical Side-Chain Polymers Post-Functionalized with High-β Chromophores Exhibiting Large Electro-Optic Property [J].
Piao, Xianqing ;
Zhang, Xianmin ;
Mori, Yuichi ;
Koishi, Masayuki ;
Nakaya, Akinari ;
Inoue, Shinichiro ;
Aoki, Isao ;
Otomo, Akira ;
Yokoyama, Shiyoshi .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2011, 49 (01) :47-54
[33]   Copper-Catalyzed Oxidative Decarboxylative Couplings of Sulfoximines and Aryl Propiolic Acids [J].
Priebbenow, Daniel L. ;
Becker, Peter ;
Bolm, Carsten .
ORGANIC LETTERS, 2013, 15 (24) :6155-6157
[34]   Decarboxylative coupling reactions: a modern strategy for C-C-bond formation [J].
Rodriguez, Nuria ;
Goossen, Lukas J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5030-5048
[35]   Tandem Heck/Decarboxylation/Heck Strategy: Protecting-Group-Free Synthesis of Symmetric and Unsymmetric Hydroxylated Stilbenoids [J].
Shard, Amit ;
Sharma, Naina ;
Bharti, Richa ;
Dadhwal, Sumit ;
Kumar, Rajesh ;
Sinha, Arun K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (49) :12250-12253
[36]   Tetrabutylammonium Iodide Catalyzed Synthesis of Allylic Ester with tert-Butyl Hydroperoxide as an Oxidant [J].
Shi, Erbo ;
Shao, Ying ;
Chen, Shulin ;
Hu, Huayou ;
Liu, Zhaojun ;
Zhang, Jie ;
Wan, Xiaobing .
ORGANIC LETTERS, 2012, 14 (13) :3384-3387
[37]   PALLADIUM-CATALYZED REARRANGEMENT OF ALLYLIC ESTERS OF ACETOACETIC ACID TO GIVE GAMMA,DELTA-UNSATURATED METHYL KETONES [J].
SHIMIZU, I ;
YAMADA, T ;
TSUJI, J .
TETRAHEDRON LETTERS, 1980, 21 (33) :3199-3202
[38]   Direct Synthesis of β-Hydroxy-α-amino Acids via Diastereoselective Decarboxylative Aldol Reaction [J].
Singjunla, Yuttapong ;
Baudoux, Jerome ;
Rouden, Jacques .
ORGANIC LETTERS, 2013, 15 (22) :5770-5773
[39]   Organocatalytic Amidation and Esterification of Aldehydes with Activating Reagents by a Cross-Coupling Strategy [J].
Tan, Bin ;
Toda, Narihiro ;
Barbas, Carlos F., III .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (50) :12538-12541
[40]   On the mechanism of the palladium(II)-catalyzed decarboxylative olefination of arene carboxylic acids. Crystallographic characterization of non-phosphine palladium(II) intermediates and observation of their stepwise transformation in Heck-like processes [J].
Tanaka, D ;
Romeril, SP ;
Myers, AG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10323-10333