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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Stereoarrayed 2,3-Disubstituted 1-Indanols via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution-Asymmetric Transfer

Andrej Emanuel Cotman¹, Barbara Modec², Barbara Mohar¹

¹National Institute of Chemistry , Hajdrihova 19 , SI-1000 Ljubljana , Slovenia.

Organic Letters

|May 11, 2018

Summary

Ruthenium(II)-catalyzed dynamic kinetic resolution provides a new method for stereoselectively reducing indanones to chiral indanols. This approach yields enantiopure diols with four contiguous chiral centers, useful for synthesizing complex molecules.

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Area of Science:

Organic Chemistry
Asymmetric Synthesis
Catalysis

Background:

Stereolabile indanones present challenges in stereoselective synthesis.
Developing efficient methods for accessing chiral alcohols is crucial in organic chemistry.

Purpose of the Study:

To develop a stereoselective reduction method for racemic 2,3-disubstituted 1-indanones.
To access enantiopure 1,4-diols with multiple contiguous chiral centers.

Main Methods:

Ruthenium(II)-catalyzed dynamic kinetic resolution (DKR) combined with asymmetric transfer hydrogenation.
Stereoselective reduction of indanones to indanols.
Friedel-Crafts benzylation for further functionalization.

Main Results:

Successfully achieved stereoselective reduction of racemic 2,3-disubstituted 1-indanones to chiral 2,3-disubstituted-1-indanols.
Generated a new class of conformationally rigid enantiopure 1,4-diols with four contiguous chiral centers.
Demonstrated the synthesis of a Pallidol analogue via diastereoselective and regioselective Friedel-Crafts benzylation.

Conclusions:

Ruthenium(II)-catalyzed DKR-asymmetric transfer hydrogenation is an effective strategy for synthesizing chiral indanols and diols.
The developed method provides practical access to complex chiral building blocks.
The study highlights the utility of these chiral diols in synthesizing complex natural product analogues.