Deshun Huang

Enantioselective Bromocyclization of Olefins Catalyzed by Chiral Phosphoric Acid

A chiral phosphoric acid catalyzed enantioselective bromocyclization of olefins is described. Various cis-, trans-, or trisubstituted γ-hydroxy-alkenes and γ-amino-alkenes can cyclize under the reaction conditions to give optically active 2-substituted tetrahydrofurans and tetrahydropyrroles in up to 91% ee.

Enantioselective Bromoaminocyclization of Allyl N-Tosylcarbamates Catalyzed by a Chiral Phosphine–Sc(OTf)3 Complex

An effective enantioselective bromoaminocyclization of allyl N-tosylcarbamates catalyzed by a chiral phosphine-Sc(OTf)3 complex is described. A wide variety of optically active oxazolidinone derivatives containing various functional groups can be obtained with high enantioselectivities.

Acid-catalyzed regioselective sulfetherification of alkenols and stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.

An efficient acid-catalyzed sulfetherification of various unsaturated alcohols with sulfenamides to form tetrahydrofurans and tetrahydropyrans regioselectively is described. Mechanistic studies have shown that the tetrahydrofurans can stereoselectively rearrange to the corresponding tetrahydropyrans.

An Acid-Catalyzed Formal Allylic C−H Oxidation of Aryl Cycloalkenes with N-Propylthiosuccinimide

A mild acid-catalyzed formal allylic C-H oxidation of aryl cycloalkenes with N-propylthiosuccinimide in the presence of various nucleophiles to generate allylic ethers, esters, and sulfonamides is described. A possible reaction mechanism has been proposed.

FeCl3/NaI-Catalyzed Allylic C–H Oxidation of Arylalkenes with a Catalytic Amount of Disulfide under Air

This paper describes a FeCl(3)/NaI-catalyzed formal allylic C-H oxidation of arylalkenes using a catalytic amount of disulfide with BnOH and 4-nitroaniline as nucleophiles and air as oxidant to form the corresponding allyl ethers and amines. A possible reaction mechanism has been proposed.

Chiral phosphoric acid catalyzed enantioselective sulfamination of amino-alkenes

This paper describes a chiral phosphoric acid-catalyzed sulfamination of amino-alkenes to form optically active 2-substituted pyrrolidines and piperidines in up to 86% ee.

Synergistic effect of additives on cyclopropanation of olefins

An efficient cyclopropanation of olefins with Zn(CH2I)2, a catalytic amount of CCl3CO2H, and 1,2-dimethoxyethane at room temperature is described. A wide variety of olefins, including acid-sensitive substrates, can be cyclopropanated in 71-99% yield.