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Asymmetric Hydrogenation of a-Amino Esters into Optically Active beta-Amino Alcohols through Dynamic Kinetic Resolution Catalyzed by Ruthenabicyclic Complexes
| Title: | Asymmetric Hydrogenation of a-Amino Esters into Optically Active beta-Amino Alcohols through Dynamic Kinetic Resolution Catalyzed by Ruthenabicyclic Complexes |
| Authors: | Ishikawa, Hiroki Browse this author | | Yurino, Taiga Browse this author →KAKEN DB | | Komatsu, Ryo Browse this author | | Gao, Ming-Yuan Browse this author | | Arai, Noriyoshi Browse this author →KAKEN DB | | Touge, Taichiro Browse this author | | Matsumura, Kazuhiko Browse this author | | Ohkuma, Takeshi Browse this author →KAKEN DB |
| Issue Date: | 7-Apr-2023 |
| Publisher: | American Chemical Society |
| Journal Title: | Organic letters |
| Volume: | 25 |
| Issue: | 13 |
| Start Page: | 2355 |
| End Page: | 2360 |
| Publisher DOI: | 10.1021/acs.orglett.3c00740 |
| PMID: | 36961208 |
| Abstract: | Racemic alpha-substituted alpha-amino esters were hydrogenated into enantioenriched beta-amino alcohols through dynamic kinetic resolution with chiral ruthenabicyclic complexes. The reaction was carried out with a substrate/catalyst molar ratio of 200-1000 under 15 atm of H-2 at 25 degrees C to afford a variety of beta-substituted beta-aminoethanols in up to 96% ee (24 examples). The mechanistic studies including deuteration experiments suggested that the reaction proceeds with 1,2-hydride migration of the a-amino acetalate intermediate into the alpha-hydroxy imine followed by the continuous reduction of the imino compound, affording the amino alcohol product. |
| Rights: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/articlesonrequest/AOR-TRF9SZAX4I5UZ2JDKM8N. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/91385 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 大熊 毅
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