Azabicyclic amino acids by stereoselective dearomatizing cyclization of the enolates of N-nicotinoyl glycine derivatives.
[Structure: see text] 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-alpha-methyl-p-methoxybenzyl group the cyclization is diastereoselective; hydrogenation and deprotection yields azabicyclic amino acids in 94:6 er.
Arnott
Gareth
G
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK.
Clayden
Jonathan
J
Hamilton
Stuart D
SD
D000596:Amino Acids / Q000737:chemistry*; D003500:Cyclization; D005998:Glycine / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D000596:Amino Acids; D005998:Glycine