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Double Asymmetric Hydrogenation of Linear β,β-Disubstituted α,β-Unsaturated Ketones into γ-Substituted Secondary Alcohols using a Dual Catalytic System
Title: | Double Asymmetric Hydrogenation of Linear β,β-Disubstituted α,β-Unsaturated Ketones into γ-Substituted Secondary Alcohols using a Dual Catalytic System |
Authors: | Arai, Noriyoshi Browse this author →KAKEN DB | Satoh, Hironori Browse this author | Komatsu, Ryo Browse this author | Ohkuma, Takeshi Browse this author →KAKEN DB |
Issue Date: | 3-Jul-2017 |
Publisher: | Wiley |
Journal Title: | Chemistry - A European Journal |
Volume: | 23 |
Issue: | 37 |
Start Page: | 8806 |
End Page: | 8809 |
Publisher DOI: | 10.1002/chem.201701527 |
PMID: | 28407316 |
Abstract: | Double asymmetric hydrogenation of linear β,β‐disubstituted α,β‐unsaturated ketones catalyzed by the DM‐SEGPHOS/DMAPEN/RuII complex with t‐C4H9OK afforded the γ‐substituted secondary alcohols in high diastereo‐ and enantioselectivities. Some mechanistic experiments suggested that two different reactive species, type (I) and (II), were reversibly formed in this catalytic system: Type (I) with the diamine ligand DMAPEN enantioselectively hydrogenated the enones into the chiral allylic alcohols, and type (II) without the diamine ligand diastereoselectively hydrogenated the allylic alcohols into the γ‐substituted secondary alcohols. This dual catalysis protocol was successfully applied to the reaction of a variety of aliphatic‐ and aromatic‐substituted enone substrates. |
Rights: | This is the peer-reviewed version of the following article: Chemistry-A European journal 23 (37) 8806-8809 2017-07-03, which has been published in final form at https://doi.org/10.1002/chem.201701527. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving. |
Type: | article (author version) |
URI: | http://hdl.handle.net/2115/71736 |
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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