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Organocatalytic Asymmetric Desymmetrization–Fragmentation of Cyclic Ketones
Author(s) -
Dickmeiss Gustav,
De Sio Vincenzo,
Udmark Jonas,
Poulsen Thomas B.,
Marcos Vanesa,
Jørgensen Karl Anker
Publication year - 2009
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.200903253
Subject(s) - desymmetrization , cinchona , thiourea , enantioselective synthesis , chemistry , umpolung , organocatalysis , fragmentation (computing) , cyclopropane , michael reaction , nucleophile , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , computer science , programming language , ring (chemistry)
A ticket to total synthesis : The title reaction of meso cyclopropane cyclopentanones and epoxycyclopentanones was catalyzed by thiourea‐containing cinchona alkaloids with good to excellent enantioselectivity (see scheme). The concept was extended to a one‐pot asymmetric desymmetrization–fragmentation–Michael addition by including a nucleophile. A kinetic resolution based on this method was also demonstrated.