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Organocatalytic Asymmetric Aziridination of Enones
Author(s) -
Pesciaioli Fabio,
De Vincentiis Francesco,
Galzerano Patrizia,
Bencivenni Giorgio,
Bartoli Giuseppe,
Mazzanti Andrea,
Melchiorre Paolo
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200803647
Subject(s) - cinchona , amine gas treating , salt (chemistry) , yield (engineering) , chemistry , organic chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , materials science , metallurgy
A primary amine derived from cinchona alkaloids as a salt with D ‐ N ‐Boc phenylglycine (Boc= tert ‐butoxycarbonyl) is an efficient catalyst for the aziridination of α,β‐unsaturated ketones. This method is effective with both linear and cyclic substrates, leading to chiral aziridines in high yield, with complete diastereoselectivity, and with very high enantioselectivity (Cbz=benzyloxycarbonyl).