Affiliation:
1. Dipartimento di Chimica e Biologia “A. Zambelli” Università di Salerno Via Giovanni Paolo II 84084 Fisciano Italy
Abstract
AbstractA first catalytic preparation of the popular antiplatelet drug (S)‐clopidogrel, known with the tradename of Plavix, has been developed in a one‐pot and innovative approach. The synthesis can be performed using commercially available ortho‐chlorobenzaldehyde, 1‐naphthylsulfonyl acetonitrile, tert‐butyl hydroperoxide (TBHP), 4,5,6,7‐tetrahydrothieno[3,2‐c]pyridine and 20 mol % of a quinidine derived organocatalyst in a single solvent. A Knoevenagel/asymmetric epoxidation/domino ring‐opening esterification (DROE) sequence enabled to obtain (S)‐clopidogrel in 61 % overall yield and 62 % ee. Fine optimization of the reaction conditions proved to be crucial to set up a selective and efficient process.
Funder
Ministero dell'Università e della Ricerca
Università degli Studi di Salerno
Subject
Organic Chemistry,Physical and Theoretical Chemistry
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