34025-30-4

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 798567-54-1 tert-butyl benzothiazolidine-3-carboxylate 
• 637-69-4 4-Methoxystyrene 

Downstream Products

• 79224-29-6 syn-2,3-dihydroxy-3-(4-methoxyphenyl)propionitrile 
• 65-85-0 benzoic acid 
• 127489-34-3 (4R,5S)-5-(4-Methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide 
• 127489-32-1 (4R,5S)-5-(4-Methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 344256-01-5 5-(4-Methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile 
• 103-82-2 phenylacetic acid 
• 82082-57-3 2,3-Dihydroxy-3-(4-methoxy-phenyl)-propionitrile 

Relevant academic research and scientific papers

Cis-dihydroxylation of alkenes with oxone catalyzed by iron complexes of a macrocyclic tetraaza ligand and reaction mechanism by ESI-MS spectrometry and DFT calculations

[FeIII(L-N4Me2)Cl2]+ (1, L-N4Me2 = N,N′-dimethyl-2,11-diaza[3.3](2,6) pyridinophane) is an active catalyst for cis-dihydroxylation of various types of alkenes with oxone at room temperature using limiting amounts of alkene substrates. In the presence of 0.7 or 3.5 mol % of 1, reactions of electron-rich alkenes, including cyclooctene, styrenes, and linear alkenes, with oxone (2 equiv) for 5 min resulted in up to >99% substrate conversion and afforded cis-diol products in up to 67% yield, with cis-diol/epoxide molar ratio of up to 16.8:1. For electron-deficient alkenes including α,β-unsaturated esters and α,β-unsaturated ketones, their reactions with oxone (2 equiv) catalyzed by 1 (3.5 mol %) for 5 min afforded cis-diols in up to 99% yield with up to >99% substrate conversion. A large-scale cis-dihydroxylation of methyl cinnamate (9.7 g) with oxone (1 equiv) afforded the cis-diol product (8.4 g) in 84% yield with 85% substrate conversion. After catalysis, the L-N4Me2 ligand released due to demetalation can be reused to react with newly added Fe(ClO4)2?4H2O to generate an iron catalyst in situ, which could be used to restart the catalytic alkene cis-dihydroxylation. Mechanistic studies by ESI-MS, isotope labeling studies, and DFT calculations on the 1-catalyzed cis-dihydroxylation of dimethyl fumarate with oxone reveal possible involvement of cis-HO-Fe V O and/or cis-O FeV O species in the reaction; the cis-dihydroxylation reactions involving cis-HO-FeV O and cis-O FeV O species both proceed by a concerted but highly asynchronous mechanism, with that involving cis-HO-FeV O being more favorable due to a smaller activation barrier.

Enantioselective reaction of α-lithiated thiazolidines as new chiral formyl anion equivalents

The reaction of lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine with benzophenone in the presence of (-)-sparteine afforded the products with up to 97% ee and 93% ee, respectively. The reaction with various aromatic and aliphatic aldehydes also afforded the products with high enantioselectivity and moderate diastereoselectivity. Each diastereomer could be converted to optically active diols. Consequently, lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine serve as chiral formyl anion equivalents. The reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway.