Scale-Up of an Enantioselective Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter 1 Inhibitor
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- 作者：Sithamalli V. Chandramouli ; Timothy A. Ayers ; Xiao-Dong Wu ; Loc T. Tran ; James H. Peers ; Rocco Disanto ; Frederick Roberts ; Narendra Kumar ; Ying Jiang ; Nakyen Choy ; Clive Pemberton ; Matthew R. Powers ; Anthony J. Gardetto ; Geoffrey A. D鈥橬etto ; Xuemin Chen ; Juan Gamboa ; Duc Ngo ; Warren Copeland ; Duane E. Rudisill ; Andrew W. Bridge ; Benoit J. Vanasse ; David J. Lythgoe
- 刊名：Organic Process Research & Development
- 出版年：2012
- 出版时间：March 16, 2012
- 年：2012
- 卷：16
- 期：3
- 页码：484-494
- 全文大小：380K
- 年卷期：v.16,no.3(March 16, 2012)
- ISSN：1520-586X
文摘
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.