1775-43-5Relevant articles and documents
Directed, regiocontrolled hydroamination of unactivated alkenes via protodepalladation
Gurak, John A.,Yang, Kin S.,Liu, Zhen,Engle, Keary M.
, p. 5805 - 5808 (2016)
A directed, regiocontrolled hydroamination of unactivated terminal and internal alkenes is reported. The reaction is catalyzed by palladium(II) acetate and is compatible with a variety of nitrogen nucleophiles. A removable bidentate directing group is used to control the regiochemistry, prevent β-hydride elimination, and stabilize the nucleopalladated intermediate, facilitating a protodepalladation event. This method affords highly functionalized amino acids in good yields with high regioselectivity.
Enantiodivergent and γ-selective asymmetric allylic amination
Wang, Jianmin,Chen, Jie,Kee, Choon Wee,Tan, Choon-Hong
supporting information; experimental part, p. 2382 - 2386 (2012/05/19)
Double agent: The title reaction using the guanidine catalyst 1 can deliver both enantiomers of the product with excellent enantioselectivity by judicious choice of the double bond geometry of the the β,γ-unsaturated carbonyl compound. Computational studies reveal the possible origin of the inversed enantioselectivity, and the potential for enantiodivergent synthesis chiral amine-containing substrates is attractive. Copyright
An ionic liquid as catalyst medium for stereoselective hydrogenations of sorbic acid with ruthenium complexes
Steines, Stephan,Wasserscheid, Peter,Driessen-Hoelscher, Birgit
, p. 348 - 354 (2007/10/03)
The ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate (bmim PF6) (6) has been studied as catalyst medium for biphasic homogeneous hydrogenations of sorbic acid (1). As catalyst we used the Cp*-ruthenium-complex [Cp*Ru(η4-CH3-CH=CH-CH=CH-COOH) (CF3SO3)] which efficiently enables the stereoselective hydrogenation of sorbic acid leading to the formation of cis-3-hexenoic acid (3) in selectivities of up to 90% with turnover frequencies of up to 1100 h-1. Compared to other biphasic systems the hydrogenation in bmim PF6 proceeds with enhanced activity. The kinetics can be described with a Michaelis-Menten-equation, and the activation energy for the whole process was determined to be EA = 78 ± 5 kJ/mol. Wiley-VCH Verlag GmbH, 2000.