180850-14-0

Upstream product

• 939-97-9 4-tert-Butylbenzaldehyde 
• 123-38-6 propionaldehyde 

Downstream Products

• 213819-66-0 (2E,4E)-1-(2-Benzyloxy-6-hydroxy-phenyl)-5-(4-tert-butyl-phenyl)-4-methyl-penta-2,4-dien-1-one 
• 117721-78-5 (E)-3-(4-(tert-butyl)phenyl)-2-methylprop-2-en-1-ol 
• 80-54-6 p-tert-butyl-α-methylhydrocinnamic aldehyde 
• 75166-31-3 (R)-(-)-3-(4-tert-Butylphenyl)-2-methylpropanal 
• 80-54-6 lilial 
• 79253-37-5 (S)-3-(4-(tert-butyl)phenyl)-2-methylpropan-1-ol 

Relevant academic research and scientific papers

Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades

Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.

Enantioselective copper-catalysed allylic alkylation of cinnamyl chlorides by Grignard reagents using chiral phosphine-phosphite ligands

The copper(I)-catalysed SN2'-type allylic substitution of E-3-aryl-allyl chlorides (cinnamyl chlorides) using Grignard reagents represents a powerful method for the synthesis of compounds carrying a benzylic stereocentre. By screening a small library of modular chiral phosphine-phosphite ligands a new copper(I)-based catalyst system was identified which allows the performance of such reactions with exceptional high degrees of regio- and enantioselectivity. Best results were obtained using TADDOLderived ligands (3 mol%), copper(I) bromide?dimethyl sulfide (CuBr?SMe2) (2.5 mol%) and methyl tert-butyl ether (MTBE) as a solvent. Various (1- alkyl-allyl)benzene derivatives were prepared with up to 99% ee (GC) in isolated yields of up to 99%. In most cases the product contained less than 3% of the linear regioisomer (except for ortho-substituted substrates). Both electron-rich and electron-deficient cinnamyl chlorides were successfully employed. The absolute configuration of the products was assigned by comparison of experimental and calculated CD spectra. The substrates were prepared from the corresponding alcohols by reaction with thionyl chloride. Initially formed mixtures of regioisomeric allylic chlorides were homogenised by treatment with CuBr?SMe2 (2.5 mol%) in the presence of triphenyl phosphine (PPh3) (3 mol%) in MTBE at low temperature to give the pure linear isomers. In reactions with methylmagnesium bromide (MeMgBr) an ortho-diphenylphosphanyl-arylphosphite ligand with an additional phenyl substituent in ortho'-position at the aryl backbone proved to be superior. In contrast, best results were obtained in the case of higher alkyl Grignard reagents (such as ethyl-, n-butyl-, isopropyl-, and 3-butenylmagnesium bromides) with a related ligand carrying an isopropyl substituent in ortho'-position. The method was tested on a multimmol scale and is suited for application in natural product synthesis.

Manufacturing of α,β-unsaturated aldehydes and ketones

The preparation of α,β-unsaturated aldehydes and ketones I is carried out by acid hydrolysis of cyclic α,β-unsaturated acetals II STR1 in the presence of saturated aldehydes.

Heterocyclics useful as fungicides and fungicidal compositions thereof

Heterocyclic compounds characterized by the formula STR1 wherein R1, R3, R4, R5, R6, X and z are as hereinafter set forth, prepared, inter alia, by reacting a compound characterized by the formula STR2 with an amine characterized by the formula STR3 wherein R1, R3, R4, R5, R6, X and Y are as hereinafter set forth, are described. The end products are useful as fungicidal agents.