Efficient stereoselective syntheses of cyclic amino acids via Michael-induced ring-closing reactions.
[reaction: see text] Zn-chelated glycine ester enolates are highly efficient nucleophiles for the synthesis of trans-methoxycarbonylcyclopropyl- and cyclobutylglycines by domino sequences of Michael additions and subsequent ring closures. They react to give the anti isomers with high yields and excellent diastereoselectivities.
Pohlman
Matthias
M
Universität des Saarlandes, Institut für Organische Chemie, Im Stadtwald, Geb. 23.2, D-66123 Saarbrücken, Germany.
Kazmaier
Uli
U
D000598:Amino Acids, Cyclic / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D003500:Cyclization; D005998:Glycine / Q000031:analogs & derivatives; D013237:Stereoisomerism
D000598:Amino Acids, Cyclic; D005998:Glycine