An efficient entry to highly substituted chiral 2-oxopiperazines from α-amino acids via iodocyclization

A short and stereoselective route for the synthesis of 2-oxopiperazines is presented starting from different naturally abundant α-amino acids. The key synthetic steps involved amide coupling, Wittig reaction, HWE olefination, aza-Michael reaction, iodocyclization. This new pathway involving first re...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 68; no. 49; pp. 10114 - 10121
Main Authors Jana, Amit Kumar, Das, Sanjit Kumar, Panda, Gautam
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.12.2012
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
POTENT
DESIGN
DIASTEREOSELECTIVE SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
KETOPIPERAZINES
DIVERSITY
FARNESYLTRANSFERASE
DUAL INHIBITORS
BICYCLIC GUANIDINES
PIPERAZINES
Michael addition
Wittig reaction
Nitrogen heterocycle
Olefination
Horner Emmons reaction
Chiral compound
Chemical coupling
Stereoselectivity
Cyclization
Aminoacid
Carboxamide
Piperazine derivatives
Chemical synthesis
Online AccessGet full text

Cover

More Information
Summary:A short and stereoselective route for the synthesis of 2-oxopiperazines is presented starting from different naturally abundant α-amino acids. The key synthetic steps involved amide coupling, Wittig reaction, HWE olefination, aza-Michael reaction, iodocyclization. This new pathway involving first report of iodocyclization to construct chiral substituted 2-oxopiperazines furnished final compounds in good yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.09.109