Jae Nyoung Kim

Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis-Hillman adducts

Abstract Tetrasubstituted pyrazole derivatives 3a – j were synthesized regioselectively in good yields from the reaction of Baylis–Hillman adducts 1a – f and hydrazine hydrochlorides 2a – d in 1,2-dichloroethane.

Synthesis of 3-quinolinecarboxylic acid esters from the Baylis–Hillman adducts of 2-halobenzaldehyde N-tosylimines

Abstract 3-Quinolinecarboxylic acid ethyl esters 4 were prepared from 1 , the Baylis–Hillman adducts of o -halobenzaldehyde N -tosylimines, in a one-pot reaction.

Synthesis of N-substituted 1,4-dihydroquinolines from the Baylis–Hillman acetates via the successive SN2′–SNAr isomerization strategy

Abstract 1,4-Dihydroquinolines 4a–e were prepared from the reaction of the Baylis–Hillman acetates of ortho-halobenzaldehydes and benzylamine or cyclohexylamine via the successive SN2′–SNAr isomerization strategy.

Synthesis of enantiomerically enriched Baylis–Hillman alcohols from their acetates: combination of kinetic resolution during the salt formation with (DHQD)2PHAL and following asymmetric induction during hydrolysis with NaHCO3 as a water surrogate

Abstract Enantiomerically enriched Baylis–Hillman alcohols 2a – d ( S ) were prepared in 25–42% yields with optical purities of 54–92% ee by using the combined concept of kinetic resolution during the salt formation of racemic Baylis–Hillman acetates 1a – d with (DHQD) 2 PHAL and the asymmetric induction during the S N 2′ type reaction with sodium bicarbonate as a water surrogate.

An expedient synthesis of 2-substituted naphthalenes from the Baylis–Hillman adducts

The reaction of 1, the acetates of the Baylis–Hillman adducts, and primary nitroalkanes 2 in the presence of potassium carbonate in N,N-dimethylformamide afforded 2-substituted naphthalenes 5 in good yields.

Synthesis of quinolines from the Baylis–Hillman acetates via the oxidative cyclization of sulfonamidyl radical as the key step

Ethyl 3-quinolinecarboxylates 5 were synthesized in good to moderate yields from the Baylis–Hillman acetates 1 via the oxidative cyclization reaction of the N-tosylamidyl radical, which was generated from the rearranged tosylamide derivatives 2 by iodobenzene diacetate and iodine.

Synthesis of ethyl 3-cyano-2-methylcinnamates and 3-cyano-2-methylcinnamonitriles from the Baylis–Hillman acetates

Abstract The reaction of the DABCO salts 2 , generated in situ from the Baylis–Hillman acetates 1 , and KCN in aqueous THF gave ethyl 3-cyano-2-methylcinnamates 4a – d and 3-cyano-2-methylcinnamonitriles 4e – f in good yields.

Synthesis of 1,3-disubstituted naphthalenes from the Baylis–Hillman acetates with the aid of manganese(III) acetate

Abstract 1,3-Disubstituted naphthalene derivatives can be easily synthesized from Baylis–Hillman acetates by successive reaction: (1) SN2′ type reaction with diethyl malonate or ethyl nitroacetate; (2) manganese(III) acetate-assisted radical cyclization and (3) aromatization with NaI/O2 system or elimination of nitrous acid.

A Convenient Synthesis of Nitrile Oxides from Aldoximes by 1-Chlorobenzotriazole

Abstract Nitrite oxides can be conveniently prepared from aldoximes utilizing 1-chlorobenzotriazole in dichloromethane. The reaction and work-up procedures are simple and the isolated yields high.

Synthesis of stereochemically defined (E)-cinnamyl alcohol derivatives from the Baylis–Hillman adducts

Abstract The reaction of the Baylis–Hillman adducts 1a – g and trifluoroacetic acid at 30–70°C gave the rearranged cinnamyl alcohols 2a – g stereoselectively in moderate yields.