Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives.
The camphor-derived tetrahydropyran (camTHP*)-desymmetrized glycinamide 1 undergoes efficient and highly diastereoselective lithium enolate Michael additions to nitro olefins, alpha,beta-unsaturated ketones, esters, and lactones. Straightforward manipulation of these products affords 3-substituted pyroglutamides and beta-aryl-alpha,gamma-diamino acid derivatives, highlighting the ease of synthesis of enantiomerically enriched, functionally dense molecules using this novel building block. [reaction: see text]
Dixon
Darren J
DJ
Department of Chemistry, University of Manchester, Manchester, M13 9PL, U.K. darren.dixon@man.ac.uk
Horan
Richard A J
RA
Monck
Nathaniel J T
NJ
Berg
Paul
P
D000596:Amino Acids / Q000138:chemical synthesis*; D002164:Camphor / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; C018556:glycine amide; D002164:Camphor; D005998:Glycine