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Stereoselective Synthesis of ( R )‐3‐Methylthalidomide by Piperidin‐2‐one Ring Assembly Approach
Author(s) -
Yadav Shyam Raj,
Tiwari Vinay Shankar,
Haq Wahajul
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22474
Subject(s) - chemistry , stereoselectivity , ring (chemistry) , yield (engineering) , enantiomer , reagent , stereochemistry , enantioselective synthesis , alanine , combinatorial chemistry , organic chemistry , amino acid , catalysis , biochemistry , materials science , metallurgy
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 . © 2015 Wiley Periodicals, Inc.