Dynamic Kinetic Resolution of α-Keto Esters via Asymmetric Transfer Hydrogenation

The dynamic kinetic resolution of β-aryl α-keto esters has been accomplished using a newly designed (arene)RuCl(monosulfonamide) transfer hydrogenation catalyst. This dynamic process generates three contiguous stereocenters with remarkable diastereoselectivity through a reduction/lactonization seque...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 134; no. 17; pp. 7329 - 7332
Main Authors Steward, Kimberly M, Gentry, Emily C, Johnson, Jeffrey S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.05.2012
Amer Chemical Soc
Subjects
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Esters - chemical synthesis
Esters - chemistry
Hydrogenation
Ketones - chemical synthesis
Ketones - chemistry
Kinetics
Physical Sciences
Science & Technology
Stereoisomerism
M-TERPHENYLS
INTERMOLECULAR STETTER REACTION
ALDEHYDES
ENANTIOSELECTIVE SYNTHESIS
KETOAMIDES
COMPLEXES
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Summary:The dynamic kinetic resolution of β-aryl α-keto esters has been accomplished using a newly designed (arene)RuCl(monosulfonamide) transfer hydrogenation catalyst. This dynamic process generates three contiguous stereocenters with remarkable diastereoselectivity through a reduction/lactonization sequence. The resulting enantioenriched, densely functionalized γ-butyrolactones are of high synthetic utility, as highlighted by several secondary derivatizations.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3027136