Asymmetric Bronsted Acid Catalysis: Catalytic Enantioselective Synthesis of Highly Biologically Active Dihydroquinazolinones

被引：204

作者：

Rueping, Magnus ^{[1
]}

Antonchick, Andrey P. ^{[1
]}

Sugiono, Erli ^{[1
]}

Grenader, Konstantin ^{[1
]}

机构：

[1] Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 05期

关键词：

antitumor agents; inhibitors; organocatalysis; phosphoric acid diester; FRIEDEL-CRAFTS REACTION; DIELS-ALDER REACTION; VINYLOGOUS MANNICH REACTION; CHIRAL PHOSPHORIC-ACID; N-ACYL IMINES; TRANSFER HYDROGENATION; 1,3-DICARBONYL COMPOUNDS; REDUCTIVE AMINATION; KINETIC RESOLUTION; ANTICANCER DRUGS;

D O I：

10.1002/anie.200804770

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Surprisingly straightforward: A metal-free, highly enantioselective Brønsted acid catalyzed condensation/addition reaction has been developed for the construction of 2,3-dihydroquinazolinones starting from 2-aminobenzamide and aldehydes (see scheme). This efficient approach provides 2,3-dihydroquinazolinones with a strong preference for the S enantiomers, which have higher biological activities than the R enantiomers. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：908 / 910

页数：3

共 50 条

[41] Dual Bronsted-acid Organocatalysis: Cooperative Asymmetric Catalysis with Combined Phosphoric and Carboxylic Acids [J].

Mitra, Raja ;

Niemeyer, Jochen .

CHEMCATCHEM, 2018, 10 (06) :1221-1234

[42] TRIP - A powerful Bronsted acid catalyst for asymmetric synthesis [J].

Adair, Gareth ;

Mukherjee, Santanu ;

List, Benjamin .

ALDRICHIMICA ACTA, 2008, 41 (02) :31-39

[43] Enantioselective Synthesis of Tropanes: Bronsted Acid Catalyzed Pseudotransannular Desymmetrization [J].

Rodriguez, Sandra ;

Uria, Uxue ;

Reyes, Efraim ;

Carrillo, Luisa ;

Tejero, Tomas ;

Merino, Pedro ;

Vicario, Jose L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (17) :6780-6784

[44] Developing Novel Organocatalyzed Aldol Reactions for the Enantioselective Synthesis of Biologically Active Molecules [J].

Bhanushali, Mayur ;

Zhao, Cong-Gui .

SYNTHESIS-STUTTGART, 2011, (12) :1815-1830

[45] Cooperative catalysis of N-heterocyclic carbene and Bronsted acid for a highly enantioselective route to unprotected spiro-indoline-pyrans [J].

Lin, Youqiang ;

Yang, Limin ;

Deng, Yue ;

Zhong, Guofu .

CHEMICAL COMMUNICATIONS, 2015, 51 (39) :8330-8333

[46] Electrostatic Basis for Enantioselective Bronsted-Acid-Catalyzed Asymmetric Ring Openings of meso-Epoxides [J].

Seguin, Trevor J. ;

Wheeler, Steven E. .

ACS CATALYSIS, 2016, 6 (04) :2681-2688

[47] Catalytic Asymmetric Piancatelli Rearrangement: BrOnsted Acid Catalyzed 4Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones [J].

Cai, Yunfei ;

Tang, Yurong ;

Atodiresei, Iuliana ;

Rueping, Magnus .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (45) :14126-14130

[48] Cooperative Catalysis with Iron and a Chiral Bronsted Acid for Asymmetric Reductive Amination of Ketones [J].

Zhou, Shaolin ;

Fleischer, Steffen ;

Jiao, Haijun ;

Junge, Kathrin ;

Beller, Matthias .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) :3451-3455

[49] 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

[50] Access to Chiral 1-Aminoindene Derivatives by Asymmetric Bronsted Acid Catalysis [J].

Wu, Xiang .

SYNLETT, 2022, 33 (06) :513-517

← 1 2 3 4 5 →