Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles
Herein, we report a practical two-step synthetic route to α-arylpyrrolidines through Suzuki–Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2020
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| Online Access: | https://hdl.handle.net/1721.1/125305 |
| _version_ | 1826201945422954496 |
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| author | Dai, Xi-Jie Engl, Oliver D. Leon Serrano, Thierry Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Dai, Xi-Jie Engl, Oliver D. Leon Serrano, Thierry Buchwald, Stephen Leffler |
| author_sort | Dai, Xi-Jie |
| collection | MIT |
| description | Herein, we report a practical two-step synthetic route to α-arylpyrrolidines through Suzuki–Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically relevant heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis of tetrahydroisoquinolines and medium-ring dibenzo-fused nitrogen heterocycles. |
| first_indexed | 2024-09-23T11:59:28Z |
| format | Article |
| id | mit-1721.1/125305 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T11:59:28Z |
| publishDate | 2020 |
| publisher | Wiley |
| record_format | dspace |
| spelling | mit-1721.1/1253052022-09-27T23:18:34Z Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles Dai, Xi-Jie Engl, Oliver D. Leon Serrano, Thierry Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Herein, we report a practical two-step synthetic route to α-arylpyrrolidines through Suzuki–Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically relevant heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis of tetrahydroisoquinolines and medium-ring dibenzo-fused nitrogen heterocycles. National Institutes of Health (U.S.) (Award R35-GM122483) National Institutes of Health (U.S.) (Grant R01-GM058160–17S1) Swiss National Science Foundation (Postdoctoral Fellowship P2EZP2_175140) 2020-05-19T13:09:23Z 2020-05-19T13:09:23Z 2019-03 2020-03-17T18:21:29Z Article http://purl.org/eprint/type/JournalArticle 1433-7851 https://hdl.handle.net/1721.1/125305 Dai, Xi-Jie et al. “Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles.” Angewandte Chemie - International Edition 58 (2019): 3407-3411 © 2019 The Author(s) en 10.1002/ANIE.201814331 Angewandte Chemie - International Edition Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf Wiley PMC |
| spellingShingle | Dai, Xi-Jie Engl, Oliver D. Leon Serrano, Thierry Buchwald, Stephen Leffler Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles |
| title | Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles |
| title_full | Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles |
| title_fullStr | Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles |
| title_full_unstemmed | Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles |
| title_short | Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles |
| title_sort | catalytic asymmetric synthesis of α arylpyrrolidines and benzo fused nitrogen heterocycles |
| url | https://hdl.handle.net/1721.1/125305 |
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