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Stereoconvergent 1,4‐Addition Reaction of 5 H ‐Oxazol‐4‐ones with E , Z Isomeric Mixture of Alkylidene β‐Ketoesters Catalyzed by Chiral Guanidines
Author(s) -
Misaki Tomonori,
Tatsumi Toshifumi,
Okamoto Tatsumasa,
Hayashi Yusuke,
Jin Nari,
Sugimura Takashi
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802271
Subject(s) - isomerization , stereoselectivity , derivatization , chemistry , catalysis , kinetic resolution , resolution (logic) , organic chemistry , medicinal chemistry , enantioselective synthesis , high performance liquid chromatography , artificial intelligence , computer science
A 1,4‐addition reaction of 5 H ‐oxazol‐4‐ones to alkylidene β‐ketoesters, which was catalyzed by using chiral guanidines via a dynamic kinetic resolution process that involved geometric isomerization of the alkylidene β‐ketoesters, was developed. This method allowed using E , Z isomeric mixture of various acyclic alkylidene β‐ketoesters to obtain the products stereoselectively. The relation between the geometry and the stereoselectivity of products was investigated, and the derivatization of the products to the corresponding α‐acyl‐γ‐lactone was performed.