Organocatalytic Asymmetric Desymmetrization–Fragmentation of Cyclic Ketones | Zendy

Dickmeiss Gustav | Zendy; De Sio Vincenzo | Zendy; Udmark Jonas | Zendy; Poulsen Thomas B. | Zendy; Marcos Vanesa | Zendy; Jørgensen Karl Anker | Zendy

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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.

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