A short formal synthesis of three epimers of penmacric acid

An extremely short formal synthesis of three epimers of penmacric acid is accomplished starting from pyroglutamate in one or two steps. Stereochemical outcome in the reaction of Li and Ti enolates of pyroglutamate with imines is found to be dependent on both chelation and steric factors. [Display om...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2010-08, Vol.66 (32), p.6167-6173
Main Authors: Sikriwal, Dimpy, Kant, Ruchir, Maulik, Prakas R., Dikshit, Dinesh K.
Format: Article
Language:English
Subjects:
Chemistry
Epimers
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Lithium enolate
Organic chemistry
Penmacric acid
Preparations and properties
Pyroglutamate
Titanium enolate
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:An extremely short formal synthesis of three epimers of penmacric acid is accomplished starting from pyroglutamate in one or two steps. Stereochemical outcome in the reaction of Li and Ti enolates of pyroglutamate with imines is found to be dependent on both chelation and steric factors. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.05.102