Cu-Catalyzed Chemoselective Preparation of 2-(Pinacolato)boron-Substituted Allylcopper Complexes and their In Situ Site-, Diastereo-, and Enantioselective Additions to Aldehydes and Ketones

Hoveyda, Amir H.; Jang, Hwanjong; Meng, Fanke; Jung, Byunghyuck

doi:10.1002/anie.201301018

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Cu-Catalyzed Chemoselective Preparation of 2-(Pinacolato)boron-Substituted Allylcopper Complexes and their In Situ Site-, Diastereo-, and Enantioselective Additions to Aldehydes and Ketones

Author(s): Fanke Meng , Hwanjong Jang , Byunghyuck Jung , Amir H. Hoveyda

Publication date Created: May 03 2013

Publication date (Print): May 03 2013

Journal: Angewandte Chemie International Edition

Publisher: Wiley-Blackwell

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A unique approach to the concise synthesis of highly optically active spirooxazolines and the discovery of a more potent oxindole-type phytoalexin analogue.

Xianxing Jiang, Yiming Cao, Yiqing Wang … (2010)

Drug-lead synthesis through rapid construction of chiral molecular complexity around the biologically relevant framework using a highly efficient strategy is a key goal of organic synthesis. Molecules bearing a spirooxindole-type framework exhibit important bioactivities. Herein, we present a highly efficient and convenient strategy that allows rapid construction of unique optically active spiro[oxazoline-3,3'-oxindole]s through the organocatalyzed asymmetric synthesis of spirocyclic thiocarbamates via an aldol reaction. Preliminary biological evaluation of several of the spirooxazolines using a model of acute neuroinflammation revealed promising antipyretic activity and provided an opportunity to discover new antipyretic agents.