Stereoselective Synthesis of (R)-3-Methylthalidomide by Piperidin-2-one Ring Assembly Approach

Shyam Raj Yadav, Vinay Shankar Tiwari, Wahajul Haq

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

A simple and stereoselective synthesis of 3-methylthalidomide, a configurationally stable thalidomide analog, is presented. Herein we describe the synthesis of (R)-3-methylthalidomide starting from (S)-alanine by piperidin-2-one ring assembly approach in high yield and enantiomeric purity without using a chiral auxiliary or reagent. Starting from (R)-alanine, the corresponding (S)-3-methylthalidomide can be prepared using the same methodology. Chirality 27:619-624, 2015.

Original languageEnglish
Pages (from-to)619-624
Number of pages6
JournalChirality
Volume27
Issue number9
DOIs
StatePublished - 1 Sep 2015
Externally publishedYes

Keywords

  • enantioretentive alkylation
  • oxazolidinone
  • teratogenic
  • thalidomide
  • tumor necrosis factor-α

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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