Quinine-thiourea catalyzed enantioselective hydrophosphonylation of trifluoromethyl 2(1H)-quinazolinones

被引：61

作者：

Xie, Hexin ^{[1
,2
]}

Song, Aiguo ^{[1
]}

Zhang, Xinshuai ^{[1
]}

Chen, Xiaobei ^{[1
]}

Li, Hao ^{[2
]}

Sheng, Chunquan ^{[3
]}

Wang, Wei ^{[1
,2
]}

机构：

[1] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

[2] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

[3] Second Mil Med Univ, Sch Pharm, Dept Med Chem, Shanghai 200433, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 09期

基金：

美国国家科学基金会;

关键词：

ALPHA-AMINO PHOSPHONATES; ASYMMETRIC-SYNTHESIS; MACROCYCLIC INHIBITORS; CONJUGATE ADDITION; HIGHLY EFFICIENT; IMINES; ACID; PHOSPHONOPEPTIDES; PENICILLOPEPSIN; FLUORINE;

D O I：

10.1039/c2cc38097h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An organocatalytic enantioselective addition reaction of cyclic ketoimines with phosphites has been developed for the first time. The process, catalyzed by Soos' quinine thiourea, affords synthetically and medicinally interesting enantioenriched trifluoromethyl dihydroquinazolinones in high yields and with high enantioselectivities.

引用

页码：928 / 930

页数：3

共 45 条

[1] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].

Akiyama, T ;

Morita, H ;

Itoh, J ;

Fuchibe, K .

ORGANIC LETTERS, 2005, 7 (13) :2583-2585

[2] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[3] Organocatalytic Asymmetric Synthesis of Organophosphorus Compounds [J].

Albrecht, Lukasz ;

Albrecht, Anna ;

Krawczyk, Henryk ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) :28-48

[4] PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].

ALLEN, JG ;

ATHERTON, FR ;

HALL, MJ ;

HASSALL, CH ;

HOLMES, SW ;

LAMBERT, RW ;

NISBET, LJ ;

RINGROSE, PS .

NATURE, 1978, 272 (5648) :56-58

[5] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].

ALLEN, MC ;

FUHRER, W ;

TUCK, B ;

WADE, R ;

WOOD, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661

[6]

Alonso E, 2000, SYNLETT, P698

[7] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID [J].

ATHERTON, FR ;

HASSALL, CH ;

LAMBERT, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) :29-40

[8]

Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine

[9] Organocatalytic Asymmetric Hydrophosphonylation/Mannich Reactions Using Thiourea, Cinchona and Bronsted Acid Catalysts [J].

Bhadury, Pinaki S. ;

Li, Hu .

SYNLETT, 2012, (08) :1108-1131

[10] SYNTHESIS OF NOVEL N-PHOSPHONOALKYL DIPEPTIDE INHIBITORS OF HUMAN COLLAGENASE [J].

BIRD, J ;

DEMELLO, RC ;

HARPER, GP ;

HUNTER, DJ ;

KARRAN, EH ;

MARKWELL, RE ;

MILESWILLIAMS, AJ ;

RAHMAN, SS ;

WARD, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (01) :158-169

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