Rhodium-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated
Carbonyl Compounds via Thiourea Hydrogen Bonding
Version 2 2016-09-12, 20:05
Version 1 2016-08-30, 19:43
Posted on 2016-08-30 - 00:00
The
strategy of secondary interaction enables enantioselectivity
for homogeneous hydrogenation. By introducing hydrogen bonding of
substrates with thiourea from the ligand, α,β-unsaturated
carbonyl compounds, such as amides and esters, are hydrogenated with
high enantiomeric excess. The substrate scope for this chemical transformation
is broad with various substituents at the β-position. Control
experiments revealed that each unit of the ligand ZhaoPhos is irreplaceable.
No nonlinear effect was observed for this Rh/ZhaoPhos-catalyzed asymmetric
hydrogenation.
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Wen, Jialin; Jiang, Jun; Zhang, Xumu (2016). Rhodium-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated
Carbonyl Compounds via Thiourea Hydrogen Bonding. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.6b01812
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AUTHORS (3)
JW
Jialin Wen
JJ
Jun Jiang
XZ
Xumu Zhang
KEYWORDS
enantioselectivityestershydrogenatednonlinear effectsubstrate scopecontrol experimentsligand ZhaoPhoschemical transformationThiourea Hydrogen BondinghydrogenationstrategyCompoundenantiomericRhodium-Catalyzed Asymmetric Hydrogenationsubstituentcarbonyl compoundsinteractionamideCarbonylβ- positionUnsaturatedthiourea