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Tunable Cinchona ‐Based Thioureas‐Catalysed Asymmetric Epoxidation to Synthetically Important Glycidic Ester Derivatives
Author(s) -
Meninno Sara,
Zullo Luca,
Overgaard Jacob,
Lattanzi Alessandra
Publication year - 2017
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.201700146
Subject(s) - chemistry , stereocenter , cinchona , thiourea , yield (engineering) , organic chemistry , enantioselective synthesis , cinchona alkaloids , combinatorial chemistry , catalysis , materials science , metallurgy
A novel class of synthetically important glycidic esters has been obtained via an asymmetric epoxidation of trans ‐α‐cyano‐α,β‐unsaturated esters catalysed by a multifunctional Cinchona alkaloid‐derived thiourea/ tert ‐butyl hydroperoxide (TBHP) system. The glycidic esters, isolated in excellent yield with complete trans ‐diastereocontrol and high enantioselectivity, proved to be versatile building blocks to access challenging small targets bearing a quaternary stereocenter.