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Preparation of homoallylic amines via a three-component coupling process
Xiaoxu Ou1, Ricardo Labes, Claudio Battilocchio
1Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK. svl1000@cam.ac.uk claudio.battilocchio@syngenta.com.
Organic & Biomolecular Chemistry
|September 6, 2018
Summary
A new three-component synthesis creates homoallylic amines from allylboron intermediates and imines. This method efficiently produces diverse compounds, including precursors for azetidines.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Homoallylic amines are valuable synthetic intermediates.
- Efficient methods for synthesizing diverse homoallylic amines are needed.
Purpose of the Study:
- To develop a novel three-component synthesis of homoallylic amines.
- To explore the scope and limitations of the developed synthetic method.
Main Methods:
- In situ generation of allylboronic species via homologation of vinyl boroxines with trimethylsilyldiazomethane.
- Trapping of the allylboron intermediate with various imines in a one-pot procedure.
Main Results:
- Successfully synthesized twenty-seven diverse homoallylic amines in moderate to high yields.
- Demonstrated tolerance of various functional groups on imine substrates (aliphatic, aromatic, heteroaromatic).
- Reported the subsequent transformation of some products into azetidines.
Conclusions:
- The developed three-component reaction provides an efficient route to functionalized homoallylic amines.
- The method is versatile and accommodates a wide range of imine substrates.
- The synthesized homoallylic amines serve as precursors for further synthetic elaborations, such as azetidine formation.
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