Aqueous enantioselective organocatalytic Diels-Alder reactions employing hydrazide catalysts. A new scaffold for organic acceleration

Mathieu Lemay; William W Ogilvie

doi:10.1021/ol051476w

Aqueous enantioselective organocatalytic Diels-Alder reactions employing hydrazide catalysts. A new scaffold for organic acceleration

Org Lett. 2005 Sep 15;7(19):4141-4. doi: 10.1021/ol051476w.

Authors

Mathieu Lemay¹, William W Ogilvie

Affiliation

¹ Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.

PMID: 16146372
DOI: 10.1021/ol051476w

Abstract

[reaction: see text] Cyclic hydrazides function as asymmetric organocatalysts in aqueous Diels-Alder reactions. The hydrazide is employed as the catalytic machinery in a compact camphor-derived framework that imparts facial selectivity to the cycloadditions. Kinetic evidence suggests the reaction involves rapid iminium formation.