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Azabicyclic Amino Acids by Stereoselective Dearomatizing Cyclization of the Enolates of N-Nicotinoyl Glycine Derivatives

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journal contribution
posted on 09.11.2006, 00:00 by Gareth Arnott, Jonathan Clayden, Stuart D. Hamilton
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.