Organocatalytic enantioselective hetero-Diels-Alder reaction of aldehydes and o-benzoquinone diimide: synthesis of optically active hydroquinoxalines

Jun-Long Li; Bo Han; Kun Jiang; Wei Du; Ying-Chun Chen

doi:10.1016/j.bmcl.2009.03.013

Organocatalytic enantioselective hetero-Diels-Alder reaction of aldehydes and o-benzoquinone diimide: synthesis of optically active hydroquinoxalines

Bioorg Med Chem Lett. 2009 Jul 15;19(14):3952-4. doi: 10.1016/j.bmcl.2009.03.013. Epub 2009 Mar 9.

Authors

Jun-Long Li¹, Bo Han, Kun Jiang, Wei Du, Ying-Chun Chen

Affiliation

¹ Key laboratory of Drug-Targeting and Drug Deliver System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, China.

PMID: 19318249
DOI: 10.1016/j.bmcl.2009.03.013

Abstract

A highly enantioselective inverse electron demand hetero-Diels-Alder reaction of o-benzoquinone diimide and aldehydes has been developed by secondary amine catalysis, giving a facile protocol to access a variety of chiral hydroquinoxalines under mild conditions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Antiviral Agents / chemical synthesis*
Antiviral Agents / chemistry
Benzoquinones / chemistry*
Catalysis
Quinoxalines / chemical synthesis*
Quinoxalines / chemistry
Stereoisomerism

Substances

Aldehydes
Antiviral Agents
Benzoquinones
Quinoxalines
2-benzoquinone