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

Gareth Arnott; Jonathan Clayden; Stuart D. Hamilton

doi:10.1021/ol062126s

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

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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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 language	English
Pages (from-to)	5325-5328
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	23
Early online date	18 Oct 2006
DOIs	https://doi.org/10.1021/ol062126s
Publication status	Published - 9 Nov 2006

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title = "Azabicyclic amino acids by stereoselective dearomatizing cyclization of the enolates of N-nicotinoyl glycine derivatives",

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.",

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T1 - Azabicyclic amino acids by stereoselective dearomatizing cyclization of the enolates of N-nicotinoyl glycine derivatives

AU - Arnott, Gareth

AU - Clayden, Jonathan

AU - Hamilton, Stuart D.

PY - 2006/11/9

Y1 - 2006/11/9

N2 - 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.

AB - 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.

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U2 - 10.1021/ol062126s

DO - 10.1021/ol062126s

M3 - Article (Academic Journal)

C2 - 17078709

AN - SCOPUS:33845257278

SN - 1523-7060

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EP - 5328

JO - Organic Letters

JF - Organic Letters

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ER -

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

Abstract

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