Microgel supported hydantoins as new chiral auxiliaries for asymmetric Mannich reactions

被引：3
作者：
Chen, Feng [1 ,2 ]
Lu, Cui-Fen [1 ,2 ]
Nie, Jun-Qi [1 ,2 ]
Yang, Gui-Chun [1 ,2 ]
Chen, Zu-Xing [1 ,2 ]
Dong, Nian-Guo [3 ]
机构：
[1] Hubei Univ, Hubei Collaborat Innovat Ctr Adv Organochem Mat, Wuhan 430062, Peoples R China
[2] Hubei Univ, Key Lab Synth & Applicat Organ Funct Mol, Minist Educ, Wuhan 430062, Peoples R China
[3] Huazhong Sci & Technol Univ, Union Hosp, Tongji Med Coll, Dept Cardiovasc Surg, Wuhan 430030, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 04期
关键词：
ALDOL REACTIONS; ORGANIC-SYNTHESIS; REAGENT;
D O I：
10.1016/j.tetasy.2015.01.008
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Four distinct microgel supported hydantoin chiral auxiliaries were prepared with four different cross-linkers and evaluated in asymmetric Mannich reactions, which proceeded in good chemical yields and with excellent stereoselectivities. Moreover, the microgel supported hydantoin chiral auxiliaries could be reused for at least four cycles without an appreciable reduction in the yield or stereoselectivity. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：180 / 185
页数：6
相关论文
共 14 条
[1]  
Danheiser R.L., 2003, Org. Synth, V80, P160
[2]   Preparation of microgel-supported chiral catalysts and their application in the asymmetric hydrogenation of aromatic ketones [J].
Deng, Jia ;
Lu, Cuifen ;
Yang, Guichun ;
Chen, Zuxing .
REACTIVE & FUNCTIONAL POLYMERS, 2012, 72 (06) :378-382
[3]   A ternary complex reagent for an asymmetric reaction of lithium ester enolates with imines [J].
Fujieda, H ;
Kanai, M ;
Kambara, T ;
Iida, A ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :2060-2061
[4]   Recent advances in the application of the Oppolzer camphorsultam as a chiral auxiliary [J].
Heravi, Majid M. ;
Zadsirjan, Vahideh .
TETRAHEDRON-ASYMMETRY, 2014, 25 (15) :1061-1090
[5]   Oxazolidinones as chiral auxiliaries in asymmetric aldol reactions applied to total synthesis [J].
Heravi, Majid M. ;
Zadsirjan, Vahideh .
TETRAHEDRON-ASYMMETRY, 2013, 24 (19) :1149-1188
[6]   SYNTHESIS OF 4-HETEROCYCLYL-HEXAHYDRO-8-METHOXYFURO[3,2-C]QUINOLINES BY LEWIS ACID-CATALYZED [4+2]CYCLOADDITION REACTION [J].
KAMETANI, T ;
FURUYAMA, H ;
FUKUOKA, Y ;
TAKEDA, H ;
SUZUKI, Y ;
HONDA, T .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (01) :185-187
[7]   Synthesis and Application of a Microgel-Supported Acylating Reagent by Coupled Ring-Opening Metathesis Polymerization and Activators Re-Generated by Electron Transfer for Atom Transfer Radical Polymerization [J].
Li, Hong ;
Pang, Zi-Bo ;
Jiao, Zhi-Feng ;
Lin, Fei .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (02) :255-259
[8]   Asymmetric and diastereoselective Mannich reactions using hydantoin as a chiral auxiliary [J].
Li, Xuan-Ran ;
Lu, Cui-Fen ;
Chen, Zu-Xing ;
Li, Yan ;
Yang, Gui-Chun .
TETRAHEDRON-ASYMMETRY, 2012, 23 (18-19) :1380-1384
[9]   2-Imidazolidinones as Chiral Auxiliaries in Asymmetric Synthesis [J].
Lu, Cuifen ;
Hu, Lei ;
Yang, Guichun ;
Chen, Zuxing .
CURRENT ORGANIC CHEMISTRY, 2012, 16 (23) :2802-2817
[10]   Synthesis and evaluation of a new non-cross-linked polystyrene supported hydantoin chiral auxiliary for asymmetric aldol reactions [J].
Lu, Guang-Jun ;
Nie, Jun-Qi ;
Chen, Zu-Xing ;
Yang, Gui-Chun ;
Lu, Cui-Fen .
TETRAHEDRON-ASYMMETRY, 2013, 24 (20) :1331-1335
12