53012-82-1Relevant academic research and scientific papers
Scale-up of an enantioselective Overman rearrangement for an asymmetric synthesis of a glycine transporter 1 inhibitor
Chandramouli, Sithamalli V.,Ayers, Timothy A.,Wu, Xiao-Dong,Tran, Loc T.,Peers, James H.,Disanto, Rocco,Roberts, Frederick,Kumar, Narendra,Jiang, Ying,Choy, Nakyen,Pemberton, Clive,Powers, Matthew R.,Gardetto, Anthony J.,Dnetto, Geoffrey A.,Chen, Xuemin,Gamboa, Juan,Ngo, Duc,Copeland, Warren,Rudisill, Duane E.,Bridge, Andrew W.,Vanasse, Benoit J.,Lythgoe, David J.
experimental part, p. 484 - 494 (2012/08/08)
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.
