Azabicyclic amino acids by stereoselective dearomatizing cyclization of the enolates of N-nicotinoyl glycine derivatives

Gareth Arnott, Jonathan Clayden*, Stuart D. Hamilton

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

38 Citations (Scopus)

Abstract

On activation by pyridine N-acylation, enolates of N-nicotinoyl and N-isonicotinoyl glycine and alanine derivatives cyclize to yield 6,5-azabicyclic or 6,4-azaspirocyclic lactams. With an N-α-methyl-p-methoxybenzyl group the cyclization is diastereoselective; hydrogenation and deprotection yields azabicyclic amino acids in 94:6 er.

Original languageEnglish
Pages (from-to)5325-5328
Number of pages4
JournalOrganic Letters
Volume8
Issue number23
Early online date18 Oct 2006
DOIs
Publication statusPublished - 9 Nov 2006

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