Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

7418747

Reference Type

Journal Article

Title

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

Author(s)

Comins, DL; Schilling, S; Zhang, Y; ,

Year

2005

Is Peer Reviewed?

Journal

Organic Letters
ISSN: 1523-7060
EISSN: 1523-7052

Publisher

AMER CHEMICAL SOC

Location

WASHINGTON

Volume

Issue

Page Numbers

95-98

Language

English

PMID

15624986

DOI

10.1021/ol047824w

Web of Science Id

WOS:000226072100024

URL

https://pubs.acs.org/doi/10.1021/ol047824w
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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.

Keywords

benzazepine derivative; carbamic acid; indole derivative; lennoxamine; unclassified drug; dioxane derivative; heterocyclic compound; indole derivative; lennoxamine; alkylation; article; asymmetric synthesis; crystal structure; demethylation; drug synthesis; high performance liquid chromatography; hydrogenation; olefination; racemization; stereochemistry; X ray analysis; chemical structure; stereoisomerism; synthesis; X ray crystallography; Crystallography, X-Ray; Dioxanes; Heterocyclic Compounds; Indoles; Models, Molecular; Stereoisomerism