1312844-96-4

Upstream product

• 30457-89-7 2-benzylallyl alcohol 
• 78-39-7 Triethyl orthoacetate 
• 20416-11-9 Ethyl 4-oxo-5-phenyl-pentanoate 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 6921-34-2 benzylmagnesium chloride 
• 14794-31-1 ethyl 3-(chloroformyl)propionate 

Downstream Products

• 1637370-62-7 C₁₄H₁₆O₄ 
• 1637370-47-8 (R)-5-benzyl-5-(iodomethyl)dihydrofuran-2(3H)-one 
• 1637370-37-6 (S)-methyl 2-benzyltetrahydrofuran-2-carboxylate 
• 1024613-09-9 (S)-5-benzyl-5-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 1282061-34-0 4-benzylpent-4-enoic acid 
• 1282060-79-0 C₁₈H₁₇NO 
• 1282061-19-1 C₁₈H₁₉NO 

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.

Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers

The copper-catalyzed enantioselective intramolecular hydroalkoxylation of unactivated alkenes for the synthesis of tetrahydrofurans, phthalans, isochromans, and morpholines from 4- and 5-alkenols is reported. The substrate scope is complementary to existing enantioselective alkene hydroalkoxylations and is broad with respect to substrate backbone and alkene substitution. The asymmetric induction and isotopic labeling studies support a polar/radical mechanism involving enantioselective oxycupration followed by C-[Cu] homolysis and hydrogen atom transfer. Synthesis of the antifungal insecticide furametpyr was accomplished.

Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

Cooperative activation with chiral nucleophilic catalysts and n-haloimides: Enantioselective iodolactonization of 4-arylmethyl-4-pentenoic acids

Chiral triaryl phosphates promote the enantioselective iodolactonization of 4-substituted 4-pentenoic acids to give the corresponding iodolactones in high yields with high enantioselectivity. N-Chlorophthalimide (NCP) is employed as a Lewis acidic activat

Pd(II)-catalyzed intramolecular amidoarylation of alkenes with molecular oxygen as sole oxidant

Stereoselective palladium-catalyzed synthesis of structurally versatile indoline derivatives, using molecular oxygen as the sole oxidant, is described. New C-N and C-C bonds form across an alkene in an intramolecular manner. The C-N bond-forming step proceeds via a syn-amidopalladation pathway. The moderate kinetic isotope effects (intramolecular KIE = 3.56) suggest that electrophilic aromatic substitution occurs in the arylation step.