Concise [4+3] cycloaddition reaction of pyrroles leading to tropinone derivatives

A concise [4+3] cycloaddition reaction of pyrroles with 2-(silyloxy)allyl cations has been developed. The oxyallyl cations stabilized with a methylthio group or geminal methyl groups were generated from the corresponding allylic alcohols under the influence of a Brönsted acid (Tf2NH), respectively....

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2012-10, Vol.53 (43), p.5725-5728
Main Authors: Fuchigami, Ryuichi, Namba, Kosuke, Tanino, Keiji
Format: Article
Language:English
Subjects:
[4+3] Cycloaddition reaction
Alcohols
Cations
Cycloaddition
Derivatives
Oxyallyl cation
Pyrroles
Sulfur-stabilized cation
Tetrahedrons
Tropinone
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A concise [4+3] cycloaddition reaction of pyrroles with 2-(silyloxy)allyl cations has been developed. The oxyallyl cations stabilized with a methylthio group or geminal methyl groups were generated from the corresponding allylic alcohols under the influence of a Brönsted acid (Tf2NH), respectively. The use of N-nosyl-protected pyrroles as the four-carbon unit was found to give tropinone derivatives in high yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.07.130