Scale-Up of an Enantioselective Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter 1 Inhibitor
Organic Process Research & Development2012Vol. 16(3), pp. 484–494
Citations Over Time
Sithamalli V. Chandramouli, Timothy A. Ayers, Xiaodong Wu, Loc T. Tran, James H. Peers, Rocco DiSanto, F. E. ROBERTS, Narendra Kumar, Ying Jiang, Nakyen Choy, Clive Pemberton, Matthew R. Powers, Anthony J. Gardetto, Geoffrey A. D’Netto, Xuemin Chen, Juan A. Gamboa, Đức Quang Ngô, Warren R. Copeland, Duane E. Rudisill, Andrew W. Bridge, Benoit Vanasse, David J. Lythgoe
Abstract
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.
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