Scale-Up of an Enantioselective Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter 1 Inhibitor
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...
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| Veröffentlicht in: | Organic process research & development 2012-03, Vol.16 (3), p.484-494 |
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| container_title | Organic process research & development |
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| creator | 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 D’Netto, Geoffrey A Chen, Xuemin Gamboa, Juan Ngo, Duc Copeland, Warren Rudisill, Duane E Bridge, Andrew W Vanasse, Benoit J Lythgoe, David J |
| description | 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. |
| doi_str_mv | 10.1021/op200378r |
| format | Article |
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Process Res. Dev</addtitle><date>2012-03-16</date><risdate>2012</risdate><volume>16</volume><issue>3</issue><spage>484</spage><epage>494</epage><pages>484-494</pages><issn>1083-6160</issn><eissn>1520-586X</eissn><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.</abstract><pub>American Chemical Society</pub><doi>10.1021/op200378r</doi><tpages>11</tpages></addata></record> |
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| title | Scale-Up of an Enantioselective Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter 1 Inhibitor |
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