Issue 99, 2014
From the journal:

Chemical Communications

Trienamine-mediated asymmetric [4+2]-cycloaddition of α,β-unsaturated ester surrogates applying 4-nitro-5-styrylisoxazoles†

Yang Li,a   Francisco Javier López-Delgado,a   Danny Kaare Bech Jørgensen,a   Rune Pagh Nielsen,a   Hao Jianga  and  Karl Anker Jørgensen*a  

* Corresponding authors

a Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark
E-mail: kaj@chem.au.dk

Abstract

Highly enantioselective organocatalytic [4+2]-cycloaddition of in situ generated trienamines with 4-nitro-5-styrylisoxazoles as α,β-unsaturated ester surrogates is presented. The synthetic utility of this strategy is demonstrated by transforming the formed cycloadducts into optically active carboxylates.

Graphical abstract: Trienamine-mediated asymmetric [4+2]-cycloaddition of α,β-unsaturated ester surrogates applying 4-nitro-5-styrylisoxazoles

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Article information

DOI
https://doi.org/10.1039/C4CC08171D
Article type
Communication
Submitted
15 Oct 2014
Accepted
30 Oct 2014
First published
30 Oct 2014

Chem. Commun., 2014,50, 15689-15691

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Trienamine-mediated asymmetric [4+2]-cycloaddition of α,β-unsaturated ester surrogates applying 4-nitro-5-styrylisoxazoles

Y. Li, F. J. López-Delgado, D. K. B. Jørgensen, R. P. Nielsen, H. Jiang and K. A. Jørgensen, Chem. Commun., 2014, 50, 15689 DOI: 10.1039/C4CC08171D

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