Highly Enantioselective Michael Addition of Malonate Derivatives to Enones Catalyzed by an N,N′-Dioxide-Scandium(III) Complex

被引：39

作者：

Chen, Donghui ^{[1
]}

Chen, Zhenling ^{[1
]}

Xiao, Xiao ^{[1
]}

Yang, Zhigang ^{[1
]}

Lin, Lili ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 28期

基金：

中国国家自然科学基金;

关键词：

asymmetric synthesis; C-C bond formation; chalcone; Michael addition; scandium; BETA-KETO-ESTERS; ORGANOCATALYTIC CONJUGATE ADDITION; CHIRAL SCANDIUM(III)-N; N'-DIOXIDE COMPLEXES; PHASE-TRANSFER CATALYSIS; LINKED-BINOL COMPLEX; DIELS-ALDER REACTION; ALPHA; BETA-UNSATURATED KETONES; QUATERNARY STEREOCENTERS; 1,3-DICARBONYL COMPOUNDS; ASYMMETRIC-SYNTHESIS;

D O I：

10.1002/chem.200901157

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective Michael addition of malonate derivatives to chalcone derivatives catalyzed by L-Ramipril acid derived N,N'-dioxide-scandium (III) complex was reported. The experiment included use of L-Ramipril acid derived N,N'-dioxide L1-nickle(II) complex to catalyze the asymmetric Michael addition of diethyl malonate to chalcone in EtOH at 35°C. The results show that 4 Å molecular sieves when added as additives result in an improved reactivity and a 95% yield without loss of enantioselectivity. Diisopropyl malonate is found to be an excellent Michael donor than the reaction accomplished in 15hr in 98% yield with 99% ee. The results also show that the electronic nature or the position of the substituents at the aromatic rings of R2 or 3 has little influence on the enantioselectivity.

引用

页码：6807 / 6810

页数：4

共 74 条

[1] Strontium-catalyzed highly enantioselective Michael additions of malonates to enones [J].