Organocatalyzed asymmetric synthesis and absolute configuration assignment of enantioenriched α-benzylaminocoumarins

被引：12

作者：

Lin, Hua ^{[1
]}

Tan, Yu ^{[1
]}

Wu, Jian-Ming ^{[1
]}

Yang, Xiao-Di ^{[2
]}

Chen, Jun-Hua ^{[1
]}

Sun, Xing-Wen ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Fudan Univ, Adv Mat Lab, Shanghai 200433, Peoples R China

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 07期

基金：

中国国家自然科学基金;

关键词：

Organocatalysis; Cinchona alkaloid; Mannich reaction; Chiral amine; Coumarin; MANNICH-TYPE REACTION; ENANTIOSELECTIVE SYNTHESIS; COUMARIN DERIVATIVES; CINCHONA ALKALOIDS; ORGANIC CATALYSIS; KETO-ESTERS; EFFICIENT; IMINES; LEVOCETIRIZINE; STEREOCENTERS;

D O I：

10.1016/j.tetlet.2014.12.138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cinchona alkaloid catalyzed asymmetric Mannich reaction of 4-hydroxycoumarins and N-p-tolylsulfinylimines was achieved to synthesize enantioenriched alpha-benzylaminocoumarins in moderate to excellent yields (up to 99%) and with moderate to good enantioselectivities (up to 83% ee). The absolute configuration of the resulting chiral amines was assigned by analysis of computational and experimental electronic circular dichroism (ECD) spectroscopies. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：913 / 917

页数：5

共 50 条

[21] Antituberculosis agent diaportheone B: synthesis, absolute configuration assignment, and anti-TB activity of its analogues
Swaroop, Pandrangi Siva
Raut, Gajanan N.
Gonnade, Rajesh G.
Verma, Priyanka
Gokhale, Rajesh S.
Reddy, D. Srinivasa
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (28) : 5385 - 5394
[22] Asymmetric total synthesis of rotenoids via organocatalyzed dynamic kinetic resolution
Perveen, Saima
Yang, Shuang
Meng, Miao
Xu, Weici
Zhang, Guoxiang
Fang, Xinqiang
COMMUNICATIONS CHEMISTRY, 2019, 2 (1)
[23] Organocatalyzed asymmetric cascade Mannich/cyclization of 3-isothiocyanato oxindoles with cyclic ketimines for the synthesis of polycyclic spiro-thioimidazolidine-oxindoles
Zhang, Chuan-Bao
Dou, Pei-Hao
Zhao, Jian-Qiang
Yuan, Wei-Cheng
TETRAHEDRON, 2020, 76 (16)
[24] Total Synthesis and Determination of the Absolute Configuration of (-)-Dolabriferol
Laclef, Sylvain
Turks, Maris
Vogel, Pierre
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8525 - 8527
[25] Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane: Synthesis of Enantioenriched α-Silyl Ketone
Kim, Jae Yeon
Kang, Byung Chul
Ryu, Do Hyun
ORGANIC LETTERS, 2017, 19 (21) : 5936 - 5939
[26] Catalytic enantioselective ethylalumination of terminal alkenes: substrate effects and absolute configuration assignment
Parfenova, Lyudmila V.
Kovyazin, Pavel V.
Tyumkina, Tatyana V.
Makrushina, Alyona V.
Khalilov, Leonard M.
Dzhemilev, Usein M.
TETRAHEDRON-ASYMMETRY, 2015, 26 (2-3) : 124 - 135
[27] Asymmetric synthesis of natural product inspired tricyclic benzopyrones by an organocatalyzed annulation reaction
Waldmann, Herbert
Khedkar, Vivek
Dueckert, Heiko
Schuemann, Markus
Oppel, Iris M.
Kumar, Kamal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (36) : 6869 - 6872
[28] Dioxindole in Asymmetric Catalytic Synthesis: Routes to Enantioenriched 3-Substituted 3-Hydroxyoxindoles and the Preparation of Maremycin A
Bergonzini, Giulia
Melchiorre, Paolo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 971 - 974
[29] Stereoselective Synthesis and Relative Configuration Assignment of Gabosine J
Angel Fresneda, Miguel
Alibes, Ramon
Font, Josep
Bayon, Pau
Figueredo, Marta
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11) : 5030 - 5035
[30] Regioselective organocatalyzed asymmetric bromolactonization of aryl acrylate-type carboxylic acids. A new approach towards enantioenriched 3-substituted isobenzofuranones
Gelat, Fabien
Coffinet, Michael
Lebrun, Stephane
Agbossou-Niedercorn, Francine
Michon, Christophe
Deniau, Eric
20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC), 2016,

← 1 2 3 4 5 →