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

Research output: Contribution to journal › Article › peer-review

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. © 2006 American Chemical Society.

Original language	English
Pages (from-to)	5325-5328
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	23
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. {\textcopyright} 2006 American Chemical Society.",

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year = "2006",

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doi = "10.1021/ol062126s",

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journal = "Organic Letters",

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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. © 2006 American Chemical Society.

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. © 2006 American Chemical Society.

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccp50nh&sid=DataCite

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccp50mg&sid=DataCite

U2 - 10.1021/ol062126s

DO - 10.1021/ol062126s

M3 - Article

VL - 8

SP - 5325

EP - 5328

JO - Organic Letters

JF - Organic Letters

SN - 1523-7052

IS - 23

ER -

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

Abstract

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