Enantiomerically Pure β-Amino Acids: A Convenient Access to Both Enantiomers of trans-2-Aminocyclohexanecarboxylic Acid

Abstract

Enantiomerically pure trans-2-aminocyclohexanecarboxylic acid is an important building block for helical β-peptides. We report here that this amino acid can be obtained from transcyclohexane-1,2-dicarboxylic acid in good yield by a simple one-pot procedure comprising cyclization to the anhydride, amide formation with ammonia, and a subsequent Hofmanntype degradation with phenyliodine(III) bis(trifluoroacetate) (PIFA) as the oxidant. The N-Fmoc-and N-BOC-protected derivatives were obtained by treatment of the amino acid with Fmoc-OSu and BOC 2 O, respectively. The N-BOC derivative could be prepared in even better overall yield by a onepot procedure leading directly from trans-cyclohexane-1,2-

Chemistry of Polyvalent Iodine

“…411 A similar BTI-induced Hofmann rearrangement has been used for the preparation of both enantiomers of trans -2-aminocyclohexanecarboxylic acid from trans -cyclohexane-1,2-dicarboxylic acid 412…”

Structure activity relationship of selective GABA uptake inhibitors

“…15 Compound 19 was N-monomethylated using the Fukuyama protocol by nosylation of the amino group giving 20 followed by methylation with methyl iodide to 21 and removal of the nosyl group yielding 22. This was then alkylated with the four different side chains 12,[16][17][18] to give 23a-d.…”

Comparison of Chiral and Racemic Forms of Zinc Cyclohexane trans‐1,2‐Dicarboxylate Frameworks: A Structural, Computational, and Calorimetric Study

“…Reactions of the racemic mixture of trans‐R , R and trans‐S , S ‐cyclohexane dicarboxylic acids (1 equiv) with zinc acetate (1 equiv) heated hydrothermally in water at 150 °C for 48 h produced single crystals of a colorless phase, 1 , which was studied by single‐crystal X‐ray diffraction. Enantiomerically pure trans ‐ R , R ‐cyclohexane dicarboxylic acid was prepared by resolution of commercially available racemic material following the procedure of Berkessel et al 18. using ( R )‐(+)‐1‐phenylethylamine.…”