An orthogonally protected β,γ′-diamino acid 6 possessing conformationally-constrained ring system was synthesized as a novel cyclic amino acid analogue. This synthesis involves as key steps chemoselective enzymatic hydrolysis of cis-piperidine-3,5-dicarboxylic ester derivative followed by efficient kinetic resolution of the partially resolved half-acid to afford the C1-symmetric piperidine-3,5-dicarboxylic acid monoester in high enantiomeric excess (>98% ee). The optically active half-acid was transformed to the cyclic amino acid via Curtius-type rearrangement.
Bibliographical noteFunding Information:
We thank the Center for Molecular Catalysis at Seoul National University through KOSEF and LGLS for generous financial support for this work. J.S.P. and C.E.Y. acknowledge the financial support in the form of BK21 fellowships.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry