Highly tunable arylated cinchona alkaloids as bifunctional catalysts

被引：38

作者：

Quigley, Cormac ^{[1
]}

Rodriguez-Docampo, Zaida ^{[1
]}

Connon, Stephen J. ^{[1
]}

机构：

[1] Univ Dublin, Sch Chem, Ctr Synth & Chem Biol, Trinity Coll, Dublin 2, Ireland

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 10期

基金：

爱尔兰科学基金会;

关键词：

DYNAMIC KINETIC RESOLUTION; ENANTIOSELECTIVE CONJUGATE ADDITION; ORGANOCATALYTIC MICHAEL ADDITION; SQUARAMIDE DERIVATIVES; ASYMMETRIC ADDITION; EFFICIENT; DESYMMETRIZATION; THIOLS; UREA; ALCOHOLYSIS;

D O I：

10.1039/c1cc14684j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the design and evaluation of a library of chiral bifunctional organocatalysts in which the distance between the catalytically active units can be systematically varied.

引用

页码：1443 / 1445

页数：3

共 39 条

[21] Cinchona Alkaloids in Asymmetric Organocatalysis [J].

Marcelli, Tommaso ;

Hiemstra, Henk .

SYNTHESIS-STUTTGART, 2010, (08) :1229-1279

[22] Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: Inversion of configuration at C9 dramatically improves catalyst performance [J].

McCooey, SH ;

Connon, SJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (39) :6367-6370

[23] Discovery and application of asymmetric reaction by multi-functional thioureas [J].

Miyabe, Hideto ;

Takemoto, Yoshiji .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (07) :785-795

[24] A highly reactive and enantioselective bifunctional organocatalyst for the methanolytic desymmetrization of cyclic anhydrides: Prevention of catalyst aggregation [J].

Oh, Sang Ho ;

Rho, Ho Sik ;

Lee, Ji Woong ;

Lee, Je Eun ;

Youk, Sung Hoon ;

Chin, Jik ;

Song, Choong Eui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (41) :7872-7875

[25] Enantioselective Alcoholysis of meso-Glutaric Anhydrides Catalyzed by Cinchona-Based Sulfonamide Catalysts [J].

Park, Sang Eun ;

Nam, Eun Hye ;

Bin Jang, Hyeong ;

Oh, Joong Suk ;

Some, Surajit ;

Lee, Yong Seop ;

Song, Choong Eui .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) :2211-2217

[26] Recent developments in dynamic kinetic resolution [J].

Pellissier, Helene .

TETRAHEDRON, 2008, 64 (08) :1563-1601

[27] Organocatalytic asymmetric addition of alcohols and Thiols to activated electrophiles: Efficient dynamic kinetic resolution and desymmetrization Protocols [J].

Peschiulli, Aldo ;

Quigley, Cormac ;

Tallon, Sean ;

Gun'ko, Yuri K. ;

Connon, Stephen J. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16) :6409-6412

[28]

Peschiulli A, 2010, NAT CHEM, V2, P380, DOI [10.1038/NCHEM.584, 10.1038/nchem.584]

[29]

Song C. E., 2009, Cinchona alkaloids in synthesis and catalysis: ligands, immobilization and organocatalysis

[30] Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts [J].

Vakulya, B ;

Varga, S ;

Csámpai, A ;

Soós, T .

ORGANIC LETTERS, 2005, 7 (10) :1967-1969

← 1 2 3 4 →