Journal article
Synthesis of Highly Functionalized Pyrrolidines via a Mild One-Pot, Three-Component 1,3-Dipolar Cycloaddition Process
Journal of organic chemistry, Vol.70(26), pp.10868-10871
12/23/2005
Handle:
https://hdl.handle.net/2376/103423
PMID: 16356011
Abstract
A simple and efficient one-pot, three-component synthesis of highly functionalized pyrrolidines via cascade imine → azomethine ylide → 1,3-dipolar cycloadditions is reported. Admixing a variety of aldehydes, dimethyl 2-aminomalonate, and electron deficient alkenes in THF leads to the clean production of pyrrolidines in good to excellent yields. The mild reaction conditions enabled the generation of previously inaccessible azomethine ylides from enolizable aldehydes. Endo selectivity was exclusive with N-phenyl maleimide and maleic anhydride. Good chemo-, regio-, and stereoselectivities were observed with methyl acrylate, though catalysis by Ag(I) was necessary with this dipolarophile.
Metrics
7 Record Views
Details
- Title
- Synthesis of Highly Functionalized Pyrrolidines via a Mild One-Pot, Three-Component 1,3-Dipolar Cycloaddition Process
- Creators
- Philip GarnerH. Ümit Kaniskan
- Publication Details
- Journal of organic chemistry, Vol.70(26), pp.10868-10871
- Academic Unit
- Chemistry, Department of
- Publisher
- American Chemical Society
- Identifiers
- 99900546530901842
- Language
- English
- Resource Type
- Journal article