Highly stereoselective additions of tin enolates to nitroalkenes and subsequent conversion of the nitro group into a nitrile.
[reaction: see text] Sn-chelated glycine ester enolates are efficient nucleophiles for highly stereoselective 1,4-additions toward nitroolefins and subsequent reductions of the nitronate intermediates formed, giving rise to amino acid nitriles.
Mendler
Barbara
B
Universität des Saarlandes, Institut für Organische Chemie, Im Stadtwald, Geb. 23.2, D-66123 Saarbrücken, Germany.
Kazmaier
Uli
U
D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis*; D009574:Nitro Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*
D000475:Alkenes; D000596:Amino Acids; D009570:Nitriles; D009574:Nitro Compounds; D009942:Organometallic Compounds; D014001:Tin; D005998:Glycine