Practical synthesis of trans-tert-butyl-2-aminocyclopentylcarbamate and resolution of enantiomers.
Optically active trans-tert-butyl-2-aminocyclopentylcarbamate (1) has potential utility as a scaffold for chiral ligands and as a modified backbone unit for peptide nucleic acids (PNAs). We have developed a short and practical synthesis of 1 via aziridine opening of tosyl-activated cyclopentene aziridine 2 and optical resolution of racemic 1 with 10-camphorsulfonic acid (CSA). The route provides ready access to multigram quantities of both enantiomers without the need for chromatography.
Xu
Qun
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Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institute of Health, DHHS, 9000 Rockville Pike, Bethesda, Maryland 20892, USA.
Appella
Daniel H
DH
D001386:Azides / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002082:Butylamines / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001386:Azides; D001388:Aziridines; D002082:Butylamines; D002219:Carbamates; D003517:Cyclopentanes; C521788:trans-tert-butyl-2-aminocyclopentylcarbamate; C033132:aziridine