Palladium-Catalyzed Asymmetric Arylation of Trifluoromethylated/Perfluoroalkylated 2-Quinazolinones with High Enantioselectivity

被引：21

作者：

Zhou, Bo ^{[1
]}

Jiang, Chunhui ^{[1
,3
]}

Gandi, Vasudeva Rao ^{[1
]}

Lu, Yixin ^{[1
]}

Hayashi, Tamio ^{[1
,2
,4
]}

机构：

[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore

[2] ASTAR, Inst Mat Res & Engn, 2 Fusionopolis Way, Singapore 138634, Singapore

[3] Jiangsu Univ Sci & Technol, Sch Environm & Chem Engn, Zhenjiang 212003, Jiangsu, Peoples R China

[4] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, 21 Nanyang Link, Singapore 637371, Singapore

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 37期

关键词：

asymmetric arylation; fluorinated molecules; palladium; phosphine-oxazoline ligand; quinazolinone; N-TERT-BUTANESULFINYL; CHIRAL DIENE LIGANDS; ARYLBORONIC ACIDS; ARYLGLYCINE DERIVATIVES; HIGH-PERFORMANCE; MANNICH REACTION; KETIMINES; IMINES; EFFICIENT; TOSYLARYLIMINES;

D O I：

10.1002/chem.201603105

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric arylation of 4-fluoroalkyl-2-quinazolinone derivatives with arylboronic acids proceeded smoothly in the presence of a cationic palladium catalyst (1 mol%) coordinated with a chiral phosphinooxazoline (phox) ligand to create the corresponding fluorine-containing arylated dihydroquinazolinones in high yields and with greater than 99% ee.

引用

页码：13068 / 13071

页数：4

共 69 条

[1] Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands [J].

Abele, Stefan ;

Inauen, Roman ;

Spielvogel, Dirk ;

Moessner, Christian .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (10) :4765-4773

[2]

Alvarez-Casao Y., 2015, ORG LETT, V17, P5104

[3]

[Anonymous], 2012, ANGEW CHE

[4]

Blacker AJ, 2000, CHEM-EUR J, V6, P353, DOI 10.1002/(SICI)1521-3765(20000117)6:2<353::AID-CHEM353>3.0.CO

[5]

2-U

[6] ASYMMETRICAL CATALYSTS .32. ENANTIOSELECTIVE PHENYLATION OF CIS-CYCLOHEXANE-1,2-DIOL AND MESO-BUTANE-2,3-DIOL [J].

BRUNNER, H ;

OBERMANN, U ;

WIMMER, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 316 (1-2) :C1-C3

[7] Enantioselective and Rapid Rh-Catalyzed Arylation of N-Tosyl- and N-Nosylaldimines in Methanol [J].

Chen, Chun-Chih ;

Gopula, Balraj ;

Syu, Jin-Fong ;

Pan, Jhih-Han ;

Kuo, Ting-Shen ;

Wu, Ping-Yu ;

Henschke, Julian P. ;

Wu, Hsyueh-Liang .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) :8077-8085

[8] Palladium(II)-Catalyzed Enantioselective Arylation of α-Imino Esters [J].

Chen, Jiayan ;

Lu, Xiaoxia ;

Lou, Wenyong ;

Ye, Yong ;

Jiang, Huanfeng ;

Zeng, Wei .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) :8541-8548

[9] Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors [J].

Corbett, JW ;

Ko, SS ;

Rodgers, JD ;

Gearhart, LA ;

Magnus, NA ;

Bacheler, LT ;

Diamond, S ;

Jeffrey, S ;

Klabe, RM ;

Cordova, BC ;

Garber, S ;

Logue, K ;

Trainor, GL ;

Anderson, PS ;

Erickson-Viitanen, SK .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (10) :2019-2030

[10] Palladimn(II)-catalyzed one-pot enantioselective synthesis of arylglycine derivatives from ethyl glyoxylate, p-toluenesulfonyl isocyanate and arylboronic acids [J].

Dai, Huixiong ;

Yang, Miao ;

Lu, Xiyan .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (02) :249-253

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