110199-18-3

Usage

Uses

Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries

InChI:InChI=1/C9H9NS2/c11-9-10-8(6-12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)/t8-/m0/s1

Upstream product

• 936741-45-6 (2R,3S)-3-hydroxy-3-(4-methoxyphenyl)-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]propan-1-one 
• 67-56-1 methanol 
• 936741-47-8 (2R,3S,4E)-3-hydroxy-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]oct-4-en-1-one 
• 140-89-6 potassium ethyl xanthogenate 
• 171877-37-5 (R)-4-phenyl-1,3-oxazolidine-2-thione 
• 56613-80-0 D-2-phenylglycinol 
• 1908-90-3 (rac)-4-phenyl-1,3-thiazolidine-2-thione 
• 1468-39-9 Isovaleric anhydride 
• 75-15-0 carbon disulfide 

Downstream Products

• 936741-32-1 2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]ethanone 
• 1217320-19-8 (R)-N-propionyl-4-phenylthiazolidine-2-thione 
• 1039757-81-7 (S)-4-phenyl-N-propanoyl-1,3-thiazolidine-2-thione 
• 1334180-43-6 (4R)-N-[(3S)-3-allyloxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 1334180-32-3 (4R)-N-[(3R)-3-allyloxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 1334180-53-8 (4R)-N-[(3S)-3-methoxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 1334180-52-7 (4R)-N-[(3R)-3-methoxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 936741-47-8 (2R,3S,4E)-3-hydroxy-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]oct-4-en-1-one 
• 936741-45-6 (2R,3S)-3-hydroxy-3-(4-methoxyphenyl)-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]propan-1-one 
• 827603-88-3 2-((S)-Diphenyl-methanesulfinyl)-1-((R)-4-phenyl-2-thioxo-thiazolidin-3-yl)-ethanone 
• 827603-84-9 2-((R)-Diphenyl-methanesulfinyl)-1-((R)-4-phenyl-2-thioxo-thiazolidin-3-yl)-ethanone 
• 153496-49-2 (4R)-3-methyl-4-phenylthiazolidin-2-one 

Relevant academic research and scientific papers

Preparation of 1,3-Thiazolidine-2-thiones by Using Potassium Ethylxanthate as a Carbon Disulfide Surrogate

A simple procedure is presented for preparing 1,3-thiazolidine-2-thiones by using potassium ethylxanthate and the corresponding β -amino alcohols as the starting materials in the presence of ethanol.

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative

Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).

Catalytic, enantioselective N-acylation of lactams and thiolactams using amidine-based catalysts

In contrast to alcohols and amines, racemic lactams and thiolactams cannot be resolved directly via enzymatic acylation or classical resolution. Asymmetric N-acylation promoted by amidine-based catalysts, particularly Cl-PIQ 2 and BTM 3, provides a convenient method for the kinetic resolution of these valuable compounds and often achieves excellent levels of enantioselectivity in this process. Density functional theory calculations indicate that the reaction occurs via N-acylation of the lactim tautomer and that cation-π interactions play a key role in the chiral recognition of lactam substrates.

Diastereoselective aldolization with N-phenylselanylacetyl derivatives

The asymmetric introduction of the phenylselanyl moiety using chiral N-phenyselanylacetyloxazolidin-2-thiones and -thiazolidin-2-thiones is reported. The diastereoselectivity is complete in favor of the syn isomer and the aldols so obtained are valuable intermediates for the synthesis of more functionalized molecules such as amino alcohols, after chemoselective activation of the selenium and substitution by nucleophilic nitrogen. Georg Thieme Verlag Stuttgart.

Compared Reactivity of a β-Aminothiol and a β-Aminoalcohol towards Phenylglyoxal

In agreement with a previous theoretical statement, (R)-N-methyl phenylglycinol and (R)-N-methyl phenylglycinethiol react with phenylglyoxal to give respectively six and five-membered heterocycles.