36935-06-5

Upstream product

• 83670-53-5 (E)-ethyl 2-(tosylimino)acetate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 1192648-97-7 C₁₆H₂₁NO₄S 
• 1192648-98-8 C₁₆H₁₉⁽²⁾H₂NO₄S 

Relevant academic research and scientific papers

Construction of α,α-disubstituted α-Amino Acid Derivatives via aza-Morita-Baylis-Hillman Reactions of 2-Aminoacrylates with Activated Olefins

A useful and convenient strategy for the synthesis of α,α-disubstituted α-amino acid (α-AA) derivatives via aza-Morita-Baylis-Hillman reaction of 2-aminoacrylates with activated olefins has been developed. A variety of α-AA derivatives containing an α-amino tertiary center were synthesized in good to excellent yields. The kinetic profiles and calculated methyl anion affinity (MAA) values were employed to rationalize the reactivities of different Michael acceptors used in the reaction.

Metal-Free Synthesis of Polysubstituted Imidazolinone Through Cyclization of Amidines with 2-Substituted Acrylates

Polysubstituted imidazolinones were synthesized in a facile metal-free cascade nucleophilic cyclization of easily available amidines and 2-substituted acrylates. This protocol is distinguished by simple, mild, and catalyst-free reaction conditions with a broad substrate scope, affording the desired products in moderate to good yields and providing an efficient strategy for synthesis of polysubstituted imidazolinone.

Synthesis of Dihydro-2-oxopyrrole (DPO) Building Blocks Catalyzed by Potassium Carbonate

A dimerization and cyclization cascade reaction of 2-sulfonaminoacrylates catalyzed by K2CO3 provides dihydro-2-oxopyrrole (DPO) derivatives. This straightforward and atom-economic transformation features a simple experimental operation with easily available starting materials, a broad substrate scope as well as good functional group tolerance. The desired DPO building blocks are obtained in moderate to good yields.

Enantioselective [3 + 2] Annulation of Enals with 2-Aminoacrylates Catalyzed by N-Heterocyclic Carbene

A novel and convenient strategy for the enantioselective synthesis of γ-lactam derivatives via N-heterocyclic carbene catalyzed formal [3 + 2] annulation of enals with 2-aminoacrylates is disclosed. This activation mode provides a complementary approach to the synthesis of various γ-lactam derivatives in good yields with excellent diastereo- and enantioselectivities. In this process, two consecutive stereocenters are constructed, and a quaternary carbon center is also established.

Access to dihydropyridinones and spirooxindoles: Application of N-heterocyclic carbene-catalyzed [3+3] annulation of enals and oxindole-derived enals with 2-aminoacrylates

A strategy for the NHC-catalyzed synthesis of dihydropyridinones and spirooxindoles has been developed via [3+3] annulation reactions of enals or isatin-derived enals with 2-aminoacrylates under oxidative conditions. In this efficient strategy, the 2-aminoacrylates served as nucleophiles. Modifying the standard base switched the carbon-carbon double bond formation from 5,6-positions to 3,4-positions to generate 5,6-dihydropyridinones and 3,4-dihydropyridinones, respectively. Meanwhile, a diverse set of spirooxindole derivatives were also synthesized in good to excellent yields.

Catalytic enantioselective formation of aziridines from α-imino esters

A new catalytic enantioselective aziridination reaction of α-imino esters with diazo compounds catalyzed by chiral Lewis acid complexes is presented. A series of N-substituted α-imino esters has been tested as substrates for the aziridination reaction using trimethylsilyldiazomethane as the carbenoid fragment donor catalyzed by various chiral complexes. Both chiral BINAP and bisoxazoline ligands, in combination with copper(I) salts in particular can catalyze the aziridination reaction leading to the cis-aziridine with up to 72 percent ee applying BINAP-copper(I) complexes as the catalyst, while the bisoxazoline-copper(I) catalysts give an aziridination reaction with lower diastereoselectivity, however, the trans-aziridine was formed in 69 percent ee. The influence of diazo compounds, Lewis acids, chiral ligands, solvents and counterion on the reaction course has been investigated and a mechanism for the reaction is discussed in which the α-imino ester coordinates to the chiral catalyst. For trimethylsilyldiazomethane, nucleophilic attack on the coordinated α-imino ester probably takes place in the case of copper(I) as the Lewis acid, while for ethyl diazoacetate the reaction course is dependent on the Lewis acid; for silver(I) a nucleophilic attack is probably also operating, while a metal-carbene intermediate is involved when copper(I) is used.