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Desymmetric Partial Reduction of Malonic Esters.

Pengwei Xu¹, Shihao Liu¹, Zhongxing Huang¹

¹State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Hong Kong 00000, China.

Journal of the American Chemical Society

|April 7, 2022

Summary

Researchers developed a new zinc-catalyzed method for the asymmetric reduction of malonic esters, yielding valuable aldehydes. This breakthrough provides a selective route to complex molecules with quaternary stereocenters.

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Area of Science:

Organic Chemistry
Asymmetric Catalysis
Synthetic Methodology

Background:

Quaternary stereocenters are crucial motifs in many bioactive molecules.
Existing methods for desymmetrization often yield alcohols, limiting further synthetic transformations.
Developing selective methods to access aldehydes from malonic esters is highly desirable.

Purpose of the Study:

To report novel conditions for the zinc-catalyzed desymmetric hydrosilylation of malonic esters.
To achieve selective reduction to aldehydes, rather than alcohols.
To enable the synthesis of diverse compounds containing quaternary stereocenters.

Main Methods:

Utilized zinc catalysis for the desymmetric hydrosilylation of disubstituted malonic esters.
Employed new pipecolinol-derived tetradentate ligands.
Optimized reaction conditions, including higher silane concentrations, to favor aldehyde formation.

Main Results:

Achieved high yields of aldehydes as the major product from various substituted malonic esters.
Obtained high aldehyde-to-alcohol ratios and excellent enantioselectivity for the aldehydes.
Demonstrated the utility of the method in synthesizing bioactive compounds and natural products.

Conclusions:

The developed method offers a powerful and selective approach for accessing aldehydes via partial reduction of malonic esters.
This strategy provides efficient access to valuable chiral building blocks with quaternary stereocenters.
The methodology expands the synthetic toolkit for constructing complex organic molecules.