The Application of a Recyclable Organocatalytic System to the Asymmetric Domino Michael/Henry Reaction in Aqueous Media

被引：51

作者：

Chintala, Poornima ^{[1
]}

Ghosh, Subrata K. ^{[1
]}

Long, Elizabeth ^{[1
]}

Headley, Allan D. ^{[1
]}

Ni, Bukuo ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, Commerce, TX 75429 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 16期

基金：

美国国家科学基金会;

关键词：

asymmetric catalysis; catalyst recycling; domino reactions; Henry reaction; Michael addition; COMPATIBLE IMINIUM ACTIVATION; DIRECT ALDOL REACTION; CONJUGATE ADDITION; ORGANIC-REACTIONS; SILYL ETHER; CASCADE CATALYSIS; HIGHLY EFFICIENT; MANNICH REACTION; ALDEHYDES; WATER;

D O I：

10.1002/adsc.201100395

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new type of pyrrolidine-based organocatalyst has been developed and found to be very effective for the domino Michael/Henry reaction in aqueous solvents. For the reaction involving pentane-1,5-dial and various nitroolefins, good yields (6585%) and excellent enantioselectivities (99%) were obtained using this catalyst. In addition, the catalyst could be recycled up to four times resulting in good yields and up to seven times with good enantioselectivity.

引用

页码：2905 / 2909

页数：5

共 82 条

[61]

Ten G.-J., 2000, SCIENCE, V287, P636

[62]

Tietze L.F., 2006, Domino Reactions in Organic Synthesis

[63] Asymmetric direct aldol reaction assisted by water and a proline-derived tetrazole catalyst [J].