Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Journal article, 2015

In organic chemistry ionic liquids (ILs) have emerged as safe and recyclable reaction solvents. In the presence of a base ILs can be deprotonated to form catalytically active N-Heterocyclic Carbenes (NHCs). Here we have used ILs as precatalysts in the addition of α,β-unsaturated aldehydes to chalcones to form 1,6-ketoesters, incorporating an anti-diphenyl moiety in a highly stereoselective fashion. The reaction has a broad substrate scope and several functional groups and heteroaromatics can be integrated into the ketoester backbone in generally good yields with maintained stereoselectivity. The reaction protocol is robust and scalable. The starting materials are inexpensive and the products can be obtained after simple filtration, avoiding solvent-demanding chromatography. Furthermore, the IL can be recycled up to 5 times without any loss of reactivity. Moreover, the 1,6-ketoester end product is a potent gelator in several hydrocarbon based solvents. The method enables rapid access to and evaluation of a new class of low molecular weight gelators (LMWGs) from recyclable and inexpensive starting materials.

gelator

NHC

organic synthesis

Issue 105

1

Ionic Liquids

6-ketoester

Chemistry

stereoselective

Author

Henrik Sundén

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Linda Ta

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Anton Axelsson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Journal of Visualized Experiments

1940-087X (ISSN)

105 e53213- e53213

Subject Categories

Organic Chemistry