Related Experiment Video
Updated: Jul 14, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Silver-catalyzed asymmetric allylation: allyltrimethoxysilane as a remarkable reagent
Hisashi Yamamoto1, Manabu Wadamoto
1Department of Chemistry, The University of Chicago, 5735 S. Ellis Avenue, Chicago, IL 60637, USA. yamamoto@uchicago.edu
Chiral silver complexes enable enantioselective allylation using allyltrimethoxysilane. This versatile method applies to aldehydes, ketones, and imines, advancing asymmetric synthesis.
Area of Science:
- Organic Chemistry
- Asymmetric Synthesis
- Organometallic Chemistry
Background:
- Recent advancements in enantioselective allylation have been reported.
- Allyltrimethoxysilane is a key reagent in these transformations.
- Metal fluorides and chiral complexes with fluoride anions are common catalytic systems.
Purpose of the Study:
- To review the development of asymmetric allylation reactions.
- To focus on the use of allyltrimethoxysilane catalyzed by chiral silver complexes.
- To highlight the versatility of this methodology.
Main Methods:
- Utilizing allyltrimethoxysilane as the allyl source.
- Employing chiral silver complexes as catalysts.
- Applying the reactions to various carbonyl compounds and imines.
Main Results:
- Demonstration of enantioselective allylation of aldehydes, ketones, and imines.
- Successful catalysis using chiral silver complexes.
- Expansion of the scope of asymmetric allylation reactions.
Conclusions:
- Chiral silver complexes are effective catalysts for enantioselective allylation with allyltrimethoxysilane.
- The methodology offers broad applicability to diverse substrates.
- This review consolidates recent progress in the field.
Related Concept Videos
Preparation and Reactions of Sulfides
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Conversion of Alcohols to Alkyl Halides
Preparation and Reactions of Thiols
Sharpless Epoxidation
