Asymmetric Synthesis of a Novel Conformationally Constrained D-Lysine Analogue with a Piperidine Skeleton

A practical asymmetric synthesis of enantiomerically pure(2R,4R)‐1‐(tert‐butoxycarbonyl)‐4‐[2‐(methoxycarbonylamino)ethyl]pipecolic acid starting from easily accessible (R)‐2‐[(S)‐1,2‐bis(benzyloxy)ethyl]‐1‐[(S)‐1‐phenylethyl]‐4‐piperidone in around 33 % overall yield has been performed. The efficie...

Full description

Saved in:
Bibliographic Details
Published in:European Journal of Organic Chemistry 2008-07, Vol.2008 (20), p.3474-3478
Main Authors: Etayo, Pablo, Badorrey, Ramón, Díaz-de-Villegas, María D., Gálvez, José A.
Format: Article
Language:English
Subjects:
Amino acids
Asymmetric ­synthesis
Lysine
Piperidines
Stereoselectivity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A practical asymmetric synthesis of enantiomerically pure(2R,4R)‐1‐(tert‐butoxycarbonyl)‐4‐[2‐(methoxycarbonylamino)ethyl]pipecolic acid starting from easily accessible (R)‐2‐[(S)‐1,2‐bis(benzyloxy)ethyl]‐1‐[(S)‐1‐phenylethyl]‐4‐piperidone in around 33 % overall yield has been performed. The efficiency of the synthetic strategy developed for the synthesis of this novel conformationally constrained D‐lysine analogue relies on the high‐yielding Wadsworth–Emmons reaction of a 2‐substituted 4‐piperidone and the diastereoselective reduction of the exocyclic C=C double bond at the 4‐position of the piperidine ring.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) The asymmetric synthesis of a novel, orthogonally protected pipecolic acid–lysinechimera in an enantiomerically pure form is reported.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200800069