Organocatalytic asymmetric annulation of 1,3-bis(alkoxycarbonyl)buta-1,3-dienes and aldehydes

Bernardo Pezzati; Mathieu F Chellat; John J Murphy; Céline Besnard; Gianna Reginato; John C Stephens; Alexandre Alexakis

doi:10.1021/ol401042b

Organocatalytic asymmetric annulation of 1,3-bis(alkoxycarbonyl)buta-1,3-dienes and aldehydes

Org Lett. 2013 Jun 21;15(12):2950-3. doi: 10.1021/ol401042b. Epub 2013 Jun 3.

Authors

Bernardo Pezzati¹, Mathieu F Chellat, John J Murphy, Céline Besnard, Gianna Reginato, John C Stephens, Alexandre Alexakis

Affiliation

¹ Department of Organic Chemistry, University of Geneva , quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland, Istituto di Chimica dei Composti Organometallici , ICCOM-CNR, via Madonna del Piano 10, Sesto Fiorentino - (Fi), 50019 Italy, Department of Chemistry, National University of Ireland Maynooth , County Kildare, Ireland, and Laboratory of Crystallography, University of Geneva , quai Ernest Ansermet 24, CH-1211 Geneva 4, Switzerland.

PMID: 23731393
DOI: 10.1021/ol401042b

Abstract

Asymmetric organocatalytic annulation of E/Z isomeric mixtures of bis(alkyl carboxylate)buta-1,3-dienes and aldehydes has been realized via enamine catalysis. In the presence of α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether, excellent stereo- and enantioselectivities were achieved for a broad spectrum of substrates.