Related Experiment Video
Updated: Jun 29, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
InCl(3)-catalyzed three-component asymmetric Mannich-type reaction in methanol
Teck-Peng Loh1, Shui-Ling Chen
1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, USA.
A one-pot Mannich-type reaction using indium(III) chloride (InCl3) catalyst in methanol yields high diastereoselectivity and product yield. The InCl3 catalyst is recyclable without loss of efficiency, offering a sustainable synthetic approach.
Area of Science:
- Organic Chemistry
- Catalysis
- Green Chemistry
Background:
- Mannich-type reactions are crucial for synthesizing valuable organic compounds.
- Developing efficient and recyclable catalysts is essential for sustainable synthesis.
- Indium(III) chloride (InCl3) has shown potential as a Lewis acid catalyst in organic transformations.
Purpose of the Study:
- To develop a one-pot, highly diastereoselective Mannich-type reaction.
- To investigate the catalytic activity and recyclability of indium(III) chloride (InCl3).
- To achieve high yields using a cost-effective and environmentally friendly method.
Main Methods:
- A one-pot Mannich-type reaction was performed in methanol.
- Indium(III) chloride (InCl3) was employed as the catalyst.
- Reaction conditions were optimized for diastereoselectivity and yield.
Main Results:
- The reaction proceeded with high diastereoselectivities.
- High yields of the desired products were obtained.
- The InCl3 catalyst was successfully recovered and reused multiple times without any loss in activity or selectivity.
Conclusions:
- The developed one-pot InCl3-catalyzed Mannich-type reaction is an efficient and selective method.
- Indium(III) chloride is a highly effective and recyclable catalyst for this transformation.
- This approach offers a sustainable and practical route for synthesizing complex organic molecules.
Related Concept Videos
Prochirality
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Radical Anti-Markovnikov Addition to Alkenes: Overview

