Carbocyclic α-amino acids: asymmetric synthesis of all four 1-amino-2-hydroxycyclohexanecarboxylic acids
1999; Elsevier BV; Volume: 10; Issue: 4 Linguagem: Inglês
10.1016/s0957-4166(99)00045-2
ISSN1362-511X
AutoresKamalesh Pai Fondekar, F.‐J. Volk, August Wilhelm Frahm,
Tópico(s)Chemical synthesis and alkaloids
ResumoStarting from racemic 2-methoxycyclohexanone and (S)- or (R)-1-phenylethylamine, respectively, the four stereoisomers of 1-amino-2-hydroxycyclohexanecarboxylic acid are obtained via an asymmetric Strecker synthesis with ee values ranging from 87 to 98%. Their stereochemistry is established by NMR methods and by X-ray analyses. Hydrogenolysis of a benzylic C–N bond by conc. sulphuric acid as well as cleavage of a methoxy ether by conc. HCl are two intriguing reactions which are observed within the five-step procedure described herein.
Referência(s)