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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

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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)

Submitter: 大熊 毅

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