Enantioselective and Diastereoselective Ir-Catalyzed Hydrogenation of α‑Substituted β‑Ketoesters via Dynamic Kinetic Resolution

An iridium/f-amphol catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti products were obtained in high yields (up to 98%) with good diastereoselectivity (up to 96:4 diastereometic ratio (dr)) and excellent...

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Published inOrganic letters Vol. 20; no. 7; pp. 1888 - 1892
Main Authors Gu, Guoxian, Lu, Jiaxiang, Yu, Ouran, Wen, Jialin, Yin, Qin, Zhang, Xumu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.04.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETO ESTER HYDROCHLORIDES
ASYMMETRIC TRANSFER HYDROGENATION
LIGANDS
REDUCTION
SYN-1,2-DIOL DERIVATIVES
AMIDO ESTERS
HYDROXY ESTERS
BAKERS-YEAST
AMINO ESTERS
ANTI
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Summary:An iridium/f-amphol catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti products were obtained in high yields (up to 98%) with good diastereoselectivity (up to 96:4 diastereometic ratio (dr)) and excellent enantioselectivity (up to >99% enantiomeric excess (ee)). A catalytic model is proposed to explain the stereoselectivity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00433