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Organocatalytic Hantzsch Type Reaction Using Aryl Hydrazines, Propiolic Acid Esters and Enals: Enantioselective Synthesis of Paroxetine
Author(s) -
Chen Lu,
Zhang Zhi,
Zu Liansuo
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000779
Subject(s) - enantioselective synthesis , chemistry , aryl , organocatalysis , organic chemistry , substrate (aquarium) , catalysis , combinatorial chemistry , scope (computer science) , alkyl , oceanography , geology , computer science , programming language
Abstract Aryl hydrazines, propiolic acid esters and enals serve as a viable substrate combination for an organocatalytic enantioselective Hantzsch type reaction. The method converts readily available starting materials into important chiral heterocycles with good to excellent yields and enantioselectivities, and has addressed the longstanding scope limitation of the classic Hantzsch reaction in the asymmetric synthesis of 2,6‐unsubstituted hydropyridines. The synthetic utility has been demonstrated by the concise enantioselective synthesis of paroxetine.