Xue-Long Hou

Desymmetric ring-opening of meso-epoxides with anilines: a simple way to chiral β-amino alcohols

Abstract Chiral β-amino alcohols were afforded by desymmetric ring-opening of meso -epoxides with anilines catalyzed by chiral Yb triflate complex in up to 80.1% ee.

Enantioselective ring opening of meso-epoxides with thiols catalyzed by a chiral (salen)Ti(IV) complex

Abstract A chiral (salen)Ti(IV) complex was an efficient catalyst in the asymmetric ring opening of meso -epoxides 1 with thiols 2 in high yields and good ee.

Synthesis of planar chiral selenide derivatives of ferrocenyl-oxazoline and their application in enantioselective palladium catalyzed allylic substitution reaction

A series of chiral selenide derivatives of ferrocenyl-oxazolines was synthesized and applied in a palladium catalyzed allylic reaction, with high enantioselectivity and moderate yield: the role of planar chirality in this reaction was also studied.

The synthesis of novel chiral N,O-ferrocenyl ligands and their application in the addition of diethylzinc to aldehydes

Abstract Novel chiral N,O -ferrocenyl ligands, in which N and O groups were attached to two different Cp rings of ferrocene, were synthesized from easily available ferrocene, and applied to the asymmetric diethylzinc addition to aldehydes. High chemical yields and good enantioselectivities (up to 90.9% ee) were obtained by using ferrocene ligand 6 .

Novel ferrocene modified P,N-ligands for enantioselective palladium-catalyzed allylic substitution reactions

Abstract Novel ferrocene modified P , N -ligands ( R , R , Sp )- 8 and ( S , S , Sp )- 9 were synthesized conveniently from enantiopure cyclohexanediamine and ( Sp )-2-phosphinoferrocenyl carboxylic acid. They were used as chiral ligands for palladium-catalyzed allylic substitutions of rac -1, 3-diphenylprop-2-enyl acetate with dimethylmalonate and benzylamine. ( R , R , Sp )- 8 was found to be a better ligand containing matched chiralities (central chirality and planar chirality) and showed a higher enantioselectivity.

Palladium-catalyzed asymmetric allylic alkylations of cycloalkenyl acetates with planar chiral phosphino-ferrocene carboxylic acids

Abstract New phosphino-ferrocene carboxylic acids with only planar chirality ( Sp )- 3 and ( Sp )- 4 have been synthesized conveniently from ( S , Sp )- 5 and ( S , Sp )- 7 . They were used as ligands in palladium-catalyzed allylic alkylation of cycloalkenyl acetates. With ligand ( Sp )- 4 , high yield and good ee were given for reactions of a series of cycloalkenyl acetates and nucleophiles.

Synthesis of novel and enantiomerically pure epoxypropylamine: a divergent route to the chiral β-adrenergic blocking agents

Abstract The chiral building block ( S )- N -benzyl- N -isopropyl-2,3-epoxypropylamine is obtained by means of chlorohydroxylation of allylamine, followed by Jacobsens hydrolytic kinetic resolution with water. A concise, divergent five-step synthesis of three β-adrenergic blocking agents in high enantiomeric excess using ( S )- N -benzyl- N -isopropyl-2,3-epoxypropylamine as the key intermediate is described.

An efficient procedure for cleavage of aziridines with various thiols promoted by ZnCl2

The ring-opening reaction of aziridines with various thiophenols and thiols catalyzed by ZnCl2 provides β-amino sulfides in high yield.

Reaction of α-carbanion of imines with N-tosylimines: a facile route to β-aminoaldehydes and 1,3-diamines

Deprotonation of aldimines by LDA, followed by trapping of the resulting carbanion with N-tosylimines and hydrolysis or reduction provides a convenient access to β-aminoaldehydes or 1,3-diamines.

Asymmetric synthesis of (2R,3S)-2,3-epoxyamides via camphor-derived sulfonium ylides

Enantiomerically enriched trans-2,3-epoxyamides 3 were prepared by the reaction of aldehydes 2 with camphor-derived chiral sulfonium ylide 1 in good yields and moderate to good ee values. The absolute configuration of the reaction product is also determined by chemical transformations.