Remote Ester Group Leads to Efficient Kinetic Resolution of Racemic Aliphatic Alcohols via Asymmetric Hydrogenation

A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method p...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 136; no. 50; pp. 17426 - 17429
Main Authors Yang, Xiao-Hui, Wang, Ke, Zhu, Shou-Fei, Xie, Jian-Hua, Zhou, Qi-Lin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.12.2014
Amer Chemical Soc
Subjects
Alcohols - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Coordination Complexes - chemistry
Esters - chemistry
Hydrogenation
Iridium - chemistry
Kinetics
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
SECONDARY ALCOHOLS
TERT-ALKYL KETONES
ACID
ACYLATION
KETOESTERS
ENANTIOSELECTIVE ACYL TRANSFER
(+)-CIVET CAT COMPOUND
DERIVATIVES
CHIRAL IRIDIUM CATALYSTS
MOLECULAR-OXYGEN
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Summary:A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method provides chiral δ-alkyl-δ-hydroxy esters and δ-alkyl-1,5-diols in good yields with high enantioselectivities even at extremely low catalyst loading (0.001 mol %).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja510990v