title: Synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid.
abstract: A synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid has been developed, thereby significantly shortening the known literature procedures for the syntheses of these unnatural amino acids. With a simple adjustment of the reaction conditions, we were able to obtain either pure cis or trans acid. Optical resolution was accomplished via diastereomeric salt formation or alternatively via chromatography on a chiral stationary phase. Finally, ab initio calculations gave an explanation for the observed cis selectivity in the initial step.
authors: Doetsch Grether AG , Falkensteinerstrasse 37, 4132 Muttenz, Switzerland.
authors: Bettina
authors: B
authors: Bakonyi
authors: Markus
authors: M
authors: Furegati
authors: Christian
authors: C
authors: Kramer
authors: Luigi
authors: L
authors: La Vecchia
authors: Flavio
authors: F
authors: Ossola
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: C586622:3-(tert-butoxycarbonyl)-3-azabicyclo(3.1.0)hexane-2-carboxylic acid; D000596:Amino Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003510:Cyclohexanes