Asymmetric Organocatalytic Michael Addition-Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

被引：4

作者：

Preegel, Gert ^{[1
]}

Silm, Estelle ^{[1
]}

Kaabel, Sandra ^{[1
,2
]}

Jarving, Ivar ^{[1
]}

Rissanen, Kari ^{[2
]}

Lopp, Margus ^{[1
]}

机构：

[1] Tallinn Univ Technol, Dept Chem & Biotechnol, Akad Tee 15, EE-12618 Tallinn, Estonia

[2] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, POB 35, Jyvaskyla 40014, Finland

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 14期

基金：

芬兰科学院;

关键词：

organocatalysis; asymmetry; diketones; dihydropyran; Michael addition; ENANTIOSELECTIVE SYNTHESIS; ENOL ETHER; CYCLOPENTANONE; TRANSFORMATION; CATALYSTS; ACCESS;

D O I：

10.1055/s-0036-1588787

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric organocatalytic Michael addition-cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and alpha, beta-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.

引用

页码：3118 / 3125

页数：8

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