Die Anlagerung von Ammoniak an Shikimisäure

Abstract

Bei der Anlagerung von Ammoniak an Shikimisäure (I) entstehen vorwiegend zwei stereoisomere Aminosäuren der Konstitution III und IV.

The Chemistry of 2-Aminocycloalkanecarboxylic Acids

“…The first selective synthesis of cis -2-ACHC 6 was performed from anhydride 4 after amidation, followed by Hofmann degradation with hypobromite. ,, This protocol was used to prepare a number of homologues and analogues, e.g. cis -2-ACPC, , cis- and trans -2-amino-4-cyclohexenecarboxylic acid, diendo -3-aminobicyclo[2.2.1hept-5-enecarboxylic acid, 3- endo -amino-5- exo -phenylbicyclo[2.2.1]heptane-2- endo -carboxylic acid, and cis -3-aminobicyclo[2.2.2]octane-2-carboxylic acid . In cases of double bond-containing derivatives, modified Hofmann degradation with hypochlorite has been applied to avoid bromine addition.…”

“…c. Michael Additions to Cycloalkenecarboxylic Acids. trans -2-ACPC and trans- 2-ACHC can be obtained selectively in moderate yields by Michael addition of ammonia to 1-cyclopentene- or 1-cyclohexenecarboxylic acid at 150−170 °C in an autoclave. ,, In the Michael addition to 1-cyclopentenecarboxylic acid, Connor and Ross reported the isolation of cis -2-ACPC besides the main trans acid , Methylamine addition to 1-cyclohexenecarboxylic acid at 140−160 °C, yielded trans -2-(methylamino)cyclohexanecarboxylic acid in 51% yield after 48 h .…”

Dielectric increments of amino acids

“…23 After distillation the mixture (25 g) was hydrogenated at 900 psi over freshly prepared Raney nickel (3 g) in absolute ethanol (200 ml) for 2.5 hr. The crude product, after filtration and removal of solvent in vacuo, was refluxed with distilled water (350 ml) for 24 hr and the solvent removed. The residual mixture of isomers was separated by fractional crystallization from water, the trans isomer being less soluble than the cis isomer.…”

2‐Azabicyclo [3.2.0] Heptane‐3‐One

“…[4] mp 212"), which gave the free amino acid (IV) (mp 202°, lit. [5] The cis-2-aminocyclopentanecarboxylic acid (IV) obtained by this synthesis is identical with the product obtained from our (j-Iactam (I).…”

“…cis-Cyclopentane-l,2-dicarboxylic acid monoamide (X) and cis-Zsamino-cyclopentanecarboxylic acid (IV) from (X) were prepared by the methods described by Plieninger and Schneider [5] .…”