Stereoselective Synthesis  of ( R )‐3‐Methylthalidomide by Piperidin‐2‐one Ring Assembly Approach | Zendy

Yadav Shyam Raj | Zendy; Tiwari Vinay Shankar | Zendy; Haq Wahajul | Zendy

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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.

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