Thiophosphoramide-Based Cooperative Catalysts for Broensted Acid Promoted Ionic Diels-Alder Reactions

Three's a crowd: The combination of a Broensted acid and a hydrogen-bond donor cocatalyst was found to promote various ionic [2+4] cycloadditions under mild reaction conditions (see scheme; Ts=4-toluenesulfonyl). Thiophosphoramides are the most effective cocatalysts because of the stronger coun...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2013-12, Vol.52 (50), p.13424-13428
Main Authors: Borovika, Alina, Tang, Pui-In, Klapman, Seth, Nagorny, Pavel
Format: Article
Language:English
Subjects:
Activation
Anions
Binding
Catalysis
Catalysts
Cycloaddition
Diels-Alder reactions
Hydrogen bonds
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Three's a crowd: The combination of a Broensted acid and a hydrogen-bond donor cocatalyst was found to promote various ionic [2+4] cycloadditions under mild reaction conditions (see scheme; Ts=4-toluenesulfonyl). Thiophosphoramides are the most effective cocatalysts because of the stronger counterion activation effect resulting from three, rather than two, hydrogen bonds involved in anion binding.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201307133