312965-07-4Relevant articles and documents
Asymmetric synthesis of a new helix-forming β-amino acid: trans-4-aminopiperidine-3-carboxylic acid
Schinnerl, Marina,Murray, Justin K.,Langenhan, Joseph M.,Gellman, Samuel H.
, p. 721 - 726 (2007/10/03)
We report a synthesis of a protected derivative of trans-4aminopiperidine-3-carboxylic acid (APiC). The route provides either enantiomer. All intermediates are purified by crystallization, and large-scale preparation is therefore possible. An analogous ro
Enantiomerically pure β-amino acids: A convenient access to both enantiomers of trans-2-aminocyclohexanecarboxylic acid
Berkessel, Albrecht,Glaubitz, Katja,Lex, Johann
, p. 2948 - 2952 (2007/10/03)
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 trans-cyclohexane-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 Hofmann-type 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 BOC2O, respectively. The N-BOC derivative could be prepared in even better overall yield by a one-pot procedure leading directly from trans-cyclohexane-1,2-dicarboxylic acid to the N-BOC-protected amino acid. Both enantiomers of the starting trans-1,2-cyclohexanedicarboxylic acid can be obtained easily and in large quantities by separating commercially available racemic trans-1,2-cyclohexanedicarboxylic acid using either (R)- or (S)-1-phenethylamine. X-ray crystallography of the diastereomerically pure salt obtained from (R)-1-phenethylamine revealed that the configuration of the diacid component is (1R,2R), and not (1S,2S) as reported in the literature. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
