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
Rok vydání:	2012
Předmět:	biology Stereochemistry Organic Chemistry Enantioselective synthesis Transfer hydrogenation Overman rearrangement Stereocenter chemistry.chemical_compound chemistry Glycine transporter 1 Hydrogenation reaction biology.protein Physical and Theoretical Chemistry Chirality (chemistry) Quinuclidine
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::284ad18f5a7d149f6244c6ddedaa3d5a https://doi.org/10.1021/op200378r Zobrazit plný text záznamu