A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from γ-butyrolactone

Benjamin E. Stephens, Fei Liu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

(Chemical Equation Presented) A fast and efficient route for diversity-oriented synthesis of 3- and 2,3-disubstituted piperidines, featuring an intramolecular nitrone cycloaddition with high regio- and diastereoselectivity, was achieved in six steps and 36-66% overall yield from commercially available γ-butyrolactone or 1,4-butanediol. A new N-alkenyl nitrone enoate was used in this intramolecular nitrone cycloaddition, and the regioselectivity, diastereoselectivity, and reversibility of this cycloaddition were investigated.

Original languageEnglish
Pages (from-to)254-263
Number of pages10
JournalJournal of Organic Chemistry
Volume74
Issue number1
DOIs
Publication statusPublished - 2 Jan 2009

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