357669-93-3

Upstream product

• 100-53-8 phenylmethanethiol 
• 123492-60-4 3-crotonoyl-1,3-oxazolidin-2-one 
• 109299-92-5 3-((E)-but-2-enoyl)oxazolidin-2-one 

Relevant academic research and scientific papers

Asymmetric conjugate addition of thiols to (E)-3-crotonoyloxazolidin-2-one by iron or cobalt/pybox catalyst

The enantioselective conjugate addition of thiols to (E)-3-crotonoyloxazolidin-2-one was effectively catalyzed by the Fe(BF4)2·6H2O/(S,S)-ip-pybox catalyst, and the addition product was obtained with up to a 95% ee. Furthe

Fe(OTf)2-Catalyzed Thia-Michael Addition Reaction: A Green Synthetic Approach to β-Thioethers

A convenient Fe(OTf)2-catalyzed Michael addition reaction of thiols to α,β-unsaturated carbonyl compounds was developed. The use of a simple procedure (EtOH, room temperature, air atmosphere) allowed to set up effective green catalytic conditions for C–S bond formation. The scope of the reaction was demonstrated using various substituted thiols and original Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 99 %). Also, the derivatization into the one-pot thia-Michael addition/oxidation reaction of 3-[3-(phenylthio)butanoyl]oxazolidin-2-one using H2O2 has proven to be efficient.

Asymmetric Sulfa-Michael Addition of α,β-Unsaturated Esters/Amides Using a Chiral N-Heterocyclic Carbene as a Noncovalent Organocatalyst

We report an asymmetric sulfa-Michael reaction of α,β-unsaturated amides and esters using a chiral N-heterocyclic carbene as the HOMO-raising organocatalyst. We discovered an interesting correlation between 13C NMR shifts of substrates and ee o

Cinchona Alkaloid Catalyzed Sulfa-Michael Addition Reactions Leading to Enantiopure β-Functionalized Cysteines

Sulfa-Michael additions to α,β-unsaturated N-acylated oxazolidin-2-ones and related α,β-unsaturated α-amino acid derivatives have been enantioselectively catalyzed by Cinchona alkaloids functionalized with a hydrogen bond donating group at the C6′ position. The series of Cinchona alkaloids includes known C6′ (thio)urea and sulfonamide derivatives and several novel species with a benzimidazole, squaramide or a benzamide group at the C6′ position. The sulfonamides were especially suited as bifunctional organocatalysts as they gave the products in very good diastereoselectivity and high enantioselectivity. In particular, the C6′ sulfonamides catalyzed the reaction with the α,β-unsaturated α-amino acid derivatives to afford the products in a diastereomeric ratio as good as 93:7, with the major isomer being formed in an ee of up to 99%. The products of the organocatalytic sulfa-Michael addition to α,β-unsaturated α-amino acid derivatives were subsequently converted in high yields to enantiopure β-functionalized cysteines suitable for native chemical ligation.

Chiral squaramide-catalyzed enantioselective conjugate michael addition of various thiols to α,β-unsaturated n-acylated oxazolidin-2-ones

A highly enantioselective sulfa-Michael addition (SMA) of various thiols to α,β-unsaturated N-acylated oxazolidinones has been achieved with a chiral squaramide catalyst under very mild reaction conditions. In addition, the conversion of the β-thio-substi