142204-61-3Relevant academic research and scientific papers
Catalytic asymmetric synthesis of chiral allylic esters
Kirsch, Stefan F.,Overman, Larry E.
, p. 2866 - 2867 (2005)
Trichloroacetimidate derivatives of prochiral (Z)-2-alken-1-ols react at room temperature with carboxylic acids to give chiral 3-acyloxy-1-alkenes in high enantiopurity in the presence of di-μ-acetatobis[(η5-(S)-(pR)-2-(2′-(4′-methylethyl)oxazolinyl)cyclopentadienyl,1-C,3′-N)(η4-tetraphenylcyclobutadiene)cobalt]dipalladium (COP-OAc) or its enantiomer. This reaction has broad scope, proceeds with predictable high stereoinduction, is accomplished at room temperature using high substrate concentrations and low catalyst loadings, and likely proceeds by a novel mechanism. Copyright
Rapid and reusable copper catalytic system for allylic oxidation of olefins in hexafluoroisopropanol as solvent
Fache, Fabienne,Piva, Olivier
, p. 2035 - 2036 (2002)
Cu2O mixed with perfluorododecanoic acid C11F23COOH and t-butyl peroxybenzoate in hexafluoroisopropanol led to a rapid and reusable catalytic system for the Kharasch-Sosnovsky reaction.
Copper-catalyzed enantioselective allylic oxidation of acyclic olefins
Zhang, Bo,Zhu, Shou-Fei,Zhou, Qi-Lin
supporting information, p. 2665 - 2668 (2013/06/26)
A copper-catalyzed asymmetric allylic oxidation of acyclic olefins has been developed. By using the complexes of copper and chiral spiro bisoxazoline ligands as catalysts, the oxidation of various acyclic olefins was accomplished with excellent regioselec
[Pd(μ-Br)(PtBu3)]2 as a highly active isomerization catalyst: Synthesis of enol esters from allylic esters
Mamone, Patrizia,Gruenberg, Matthias F.,Fromm, Andreas,Khan, Bilal A.,Goossen, Lukas J.
, p. 3716 - 3719 (2012/09/08)
The dimeric Pd(I)-complex [Pd(μ-Br)(PtBu3)] 2 was found to be highly active for catalyzing double-bond migration in various substrates such as unsaturated ethers, alcohols, amides, and arenes, under mild conditions. It efficiently mediates the conversion of allylic esters into enol esters, rather than inserting into the allylic C-O bond. The broad applicability of this reaction was demonstrated with the synthesis of 22 functionalized enol esters.
Redox-neutral atom-economic rhodium-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters
Lumbroso, Alexandre,Koschker, Philipp,Vautravers, Nicolas R.,Breit, Bernhard
supporting information; experimental part, p. 2386 - 2389 (2011/05/04)
A new method for the preparation of a wide range of branched allylic esters from terminal alkynes that proceeds via a redox-neutral propargylic CH activation employing a rhodium(I)/DPEphos catalyst is reported.
Iridium-catalyzed kinetic asymmetric transformations of racemic allylic benzoates
Stanley, Levi M.,Bai, Chen,Ueda, Mitsuhiro,Hartwig, John F.
supporting information; experimental part, p. 8918 - 8920 (2010/08/21)
Versatile methods for iridium-catalyzed, kinetic asymmetric substitution of racemic, branched allylic esters are reported. These reactions occur with a variety of aliphatic, aryl, and heteroaryl allylic benzoates to form the corresponding allylic substitution products in high yields (74-96%) with good to excellent enantioselectivity (84-98% ee) with a scope that encompasses a range of anionic carbon and heteroatom nucleophiles. These kinetic asymmetric processes occur with distinct stereochemical courses for racemic aliphatic and aromatic allylic benzoates, and the high reactivity of branched allylic benzoates enables enantioselective allylic substitutions that are slow or poorly selective with linear allylic electrophiles.
Catalytic asymmetric synthesis of chiral allylic esters
Cannon, Jeffrey S.,Kirsch, Stefan F.,Overman, Larry E.
supporting information; experimental part, p. 15185 - 15191 (2010/12/25)
A broadly useful catalytic enantioselective synthesis of branched allylic esters from prochiral (Z)-2-alkene-1-ols has been developed. The starting allylic alcohol is converted to its trichloroacetimidate intermediate by reaction with trichloroacetonitrile, either in situ or in a separate step, and this intermediate undergoes clean enantioselective SN2′ substitution with a variety of carboxylic acids in the presence of the palladium(II) catalyst (Rp,S)-di-μ-acetatobis[(η5- 2-(2′-(4′-methylethyl)oxazolinyl)cyclopentadienyl-1-C,3′-N) (η4-tetraphenylcyclobutadiene)cobalt]dipalladium, (R p,S)-[COP-OAc]2, or its enantiomer. The scope and limitations of this useful catalytic asymmetric allylic esterification are defined.
Iridium-catalyzed enantioselective synthesis of allylic alcohols: Silanolates as hydroxide equivalents
Lyothier, Isabelle,Defieber, Christian,Carreira, Erick M.
, p. 6204 - 6207 (2007/10/03)
(Chemical Equation Presented) Masked hydroxide: A highly regio- and enantioselective Ir-catalyzed allylic etherification of acyclic, achiral allylic carbonates can be achieved by using potassium silanolates as nucleophiles. The use of these hydroxide equi
A New Approach to the Synthesis of Chiral Vinyl Carbinols from 2,3-Epoxy Alcohols
Martin, Victor S.,Ode, Jesus M.,Palazon, Jose M.,Soler, Marcos A.
, p. 573 - 580 (2007/10/02)
The regioselective opening with benzoic acid of 2,3-epoxy alcohols obtained from the asymmetric epoxidation of 2,3-allylic alcohols, and deoxygenation of the resulting diol benzoates provides an effective, general and simple method to convert chiral 2,3-epoxy alcohols, into vinyl carbinols without the loss of any optical purity.
