Scale-Up of an Enantioselective Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter 1 Inhibitor
Autor: | Vanasse Benoit J, Loc T. Tran, Juan Gamboa, Xuemin Chen, Timothy A. Ayers, Xiaodong Wu, Nakyen Choy, Rocco Disanto, Duane E. Rudisill, Duc P. Ngo, Ying Jiang, Geoffrey A. D'netto, Gardetto Anthony J, Sithamalli V. Chandramouli, David J. Lythgoe, Frederick Roberts, Narendra Kumar, Matthew R. Powers, Andrew W. Bridge, James H. Peers, Warren Copeland, Clive Pemberton |
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Rok vydání: | 2012 |
Předmět: | |
Zdroj: | Organic Process Research & Development. 16:484-494 |
ISSN: | 1520-586X 1083-6160 |
Popis: | An enantioselective Overman 3,3-sigmatropic rearrangement on a quinuclidine skeleton was developed for the pilot-plant synthesis of a glycine transporter 1 inhibitor. The first stereocenter was produced by a Ru-catalyzed asymmetric transfer hydrogenation process followed by chirality transfer using the Overman rearrangement. The second stereocenter was generated by a diastereoselective hydrogenation reaction. |
Databáze: | OpenAIRE |
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