Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine

Daniel L Comins; Stefan Schilling; Yanchen Zhang

doi:10.1021/ol047824w

Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine

Org Lett. 2005 Jan 6;7(1):95-8. doi: 10.1021/ol047824w.

Authors

Daniel L Comins¹, Stefan Schilling, Yanchen Zhang

Affiliation

¹ Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA. daniel_comins@nscu.edu

PMID: 15624986
DOI: 10.1021/ol047824w

Abstract

An anionic chiral auxiliary mediated asymmetric alkylation of carbamate 2 provides 3-substituted isoindolinones 4 in high ee. This methodology was used in the first asymmetric synthesis of (+)-lennoxamine.

Publication types

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

MeSH terms

Crystallography, X-Ray
Dioxanes / chemical synthesis*
Heterocyclic Compounds / chemical synthesis*
Indoles / chemical synthesis*
Models, Molecular
Stereoisomerism

Substances

Dioxanes
Heterocyclic Compounds
Indoles
lennoxamine