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Chemoselectivity Control in the Asymmetric Hydrogenation of γ- and δ-Keto Esters into Hydroxy Esters or Diols

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Title: Chemoselectivity Control in the Asymmetric Hydrogenation of γ- and δ-Keto Esters into Hydroxy Esters or Diols
Authors: Arai, Noriyoshi Browse this author →KAKEN DB
Namba, Takanori Browse this author
Kawaguchi, Kei Browse this author
Matsumoto, Yuki Browse this author
Ohkuma, Takeshi Browse this author →KAKEN DB
Keywords: asymmetric catalysis
keto esters
Issue Date: 26-Jan-2018
Publisher: Wiley
Journal Title: Angewandte Chemie International Edition
Volume: 57
Issue: 5
Start Page: 1386
End Page: 1389
Publisher DOI: 10.1002/anie.201711363
PMID: 29205740
Abstract: The asymmetric hydrogenation of aromatic γ‐ and δ‐keto esters into optically active hydroxy esters or diols under the catalysis of a novel DIPSkewphos/3‐AMIQ–RuII complex was studied. Under the optimized conditions (8 atm H2 , Ru complex/t‐C4H9OK=1:3.5, 25 °C) the γ‐ and δ‐hydroxy esters (including γ‐lactones) were obtained quantitatively with 97–99 % ee. When the reaction was conducted under somewhat harsh conditions (20 atm H2 , [t‐C4H9OK]=50 mm, 40 °C), the 1,4‐ and 1,5‐diols were obtained predominantly with 95–99 % ee. The reactivity of the ester group was notably dependent on the length of the carbon spacer between the two carbonyl moieties of the substrate. The reaction of β‐ and ϵ‐keto esters selectively afforded the hydroxy esters regardless of the reaction conditions. This catalyst system was applied to the enantioselective and regioselective (for one of the two ester groups) hydrogenation of a γ‐ϵ‐diketo diester into a trihydroxy ester.
Rights: This is the peer-reviewed version of the following article: Angewandte chemie-international edition 57 (5) 1386-1389 2018-01-26, which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving.
Type: article (author version)
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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