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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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Updated: Jul 12, 2026

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

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

Published on: February 16, 2020

Dynamic Kinetic Resolution-Based Asymmetric Hydrogenation of Pyridines.

Zhiwen Nie¹, Nianxin Rong¹, Feng Xu¹

¹Faculty of Pharmaceutical Sciences, Shenzhen University of Advanced Technology, Shenzhen 518107, China.

Journal of the American Chemical Society

|July 10, 2026

Summary

This study introduces a new iridium-catalyzed method for synthesizing chiral piperidines directly from pyridines. The dynamic kinetic resolution approach achieves high stereocontrol without preactivation, simplifying access to valuable pharmaceutical building blocks.

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Last Updated: Jul 12, 2026

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

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Area of Science:

Organic Chemistry
Asymmetric Catalysis
Medicinal Chemistry

Background:

Chiral piperidines are essential structural motifs in numerous pharmaceuticals.
Efficient and stereoselective synthesis of chiral piperidines from simple precursors is a significant synthetic challenge.
Existing methods for pyridine hydrogenation often require preactivation, have limited substrate scope, and struggle with stereocontrol.

Purpose of the Study:

To develop a direct asymmetric hydrogenation strategy for racemic C2-substituted pyridines.
To overcome limitations of existing methods, including catalyst deactivation and poor stereochemical diversity.
To enable the synthesis of complex chiral piperidines with high enantioselectivity and diastereoselectivity.

Main Methods:

Development of an iridium-catalyzed dynamic kinetic resolution (DKR) strategy.
In situ generation of hydrogen iodide to transiently activate the pyridine substrate.
Direct asymmetric hydrogenation of racemic C2-substituted pyridines without prior activation.

Main Results:

Successful direct asymmetric hydrogenation of racemic C2-substituted pyridines.
The reaction proceeds under mild conditions with a broad substrate scope.
High enantioselectivity (up to >99% ee) and diastereoselectivity (up to >20:1 dr) were achieved, yielding chiral piperidines with vicinal stereocenters.

Conclusions:

The reported iridium-catalyzed DKR strategy provides an efficient route to chiral piperidines.
This method overcomes key challenges in pyridine hydrogenation, offering improved scope and stereochemical control.
The approach facilitates the synthesis of valuable chiral piperidine building blocks for pharmaceutical applications.