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N-bromosuccinimide promoted ring expansion reactions: Diastereoselective formation of functionalized azaspirocyclic cyclopentanones

TitleN-bromosuccinimide promoted ring expansion reactions: Diastereoselective formation of functionalized azaspirocyclic cyclopentanones
Publication TypeJournal Article
Year of Publication2003
AuthorsHurley, PB, Dake, GR
JournalSynlett
Pagination2131-2134
Date PublishedNov
Type of ArticleArticle
ISBN Number0936-5214
Keywordsbromine, CONSTRUCTION, entry, HALICHLORINE, ION, KETONES, PINNAIC ACID, piperidines, REDUCTION, ring expansion, spiro compounds, SPIROCYCLIC CORE, STEREOSELECTIVE
Abstract

N-Bromosuccinimide (NBS) induces ring enlargements of 2-(1-hydroxycyclobutyl)-p-toluenesulfonylenamides such as 1. These high yielding reactions typically occur with good diastereoselectivity. This ring expansion protocol under neutral conditions forms compounds that are potentially versatile intermediates for the construction of spirocycle-containing alkaloids.

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