93863-05-9

Upstream product

• 186581-53-3 diazomethane 
• 64-19-7 acetic acid 
• 98-83-9 isopropenylbenzene 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 6399-81-1 triphenylphosphine hydrobromide 
• 40949-94-8 potassium hexamethylsilazane 
• 1445-45-0 Trimethyl orthoacetate 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 5747-06-8 4-phenylpent-4-enoic acid 
• 74-88-4 methyl iodide 
• 118453-36-4 dimethyl 2-(2'-bromoallyl)malonate 
• 2051-95-8 succinylbenzene 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 67-56-1 methanol 

Downstream Products

• 5747-06-8 4-phenylpent-4-enoic acid 
• 1254701-62-6 (S)-5-(bromomethyl)-dihydro-5-phenylfuran-2(3H)-one 
• 1217263-84-7 (R)-5-(bromomethyl)-dihydro-5-phenylfuran-2(3H)-one 

Relevant academic research and scientific papers

Gold(I)-catalyzed cascade cycloadditions between allenamides and carbonyl-tethered alkenes: An enantioselective approach to oxa-bridged medium-sized carbocycles

Gold standard: Allenamides react with aldehydes or ketones having γ, δ, or ε alkenyl groups, upon activation with suitable gold catalysts, to provide oxa-bridged systems containing seven- to nine-membered carbocycles, in a formal cascade cycloaddition. By using chiral phosphoramidite/gold or bisphosphine/gold catalysts it is possible to obtain the oxa-bridged seven- and eight-membered rings with good to high enantioselectivity. Copyright

Biomimetic Total Synthesis of Enterocin

The first chemical total synthesis of the highly oxygenated polyketide enterocin has been accomplished. The key step of the synthesis was a late-stage biomimetic reaction cascade involving two intramolecular aldol reactions in which each step proceeded in 52 % yield (averaged) and which established four of the seven stereogenic centers. The pivotal precursor for the cascade reaction was assembled from three readily available building blocks. A chiral dithioacetal with two stereogenic centers originating from L-arabinose represented the core fragment to both ends of which the other building blocks were attached by aldol reactions. The remaining stereogenic center was installed by Davis oxygenation immediately prior to the key step.

Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons

Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.

Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings

The synthesis of novel, highly functionalized, C 2 -symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides

Electrophilic Bromolactonization of Cyclopropyl Carboxylic Acids Using Lewis Basic Sulfide Catalyst

A highly facile and efficient electrophilic bromolactonization of cyclopropylcarboxylic acids could be effected by a Lewis basic sulfide catalyst. Mechanistic studies performed revealed that the cyclopropane substrates could undergo radical bromination upon exposure to light, yielding a mixture of regioisomers. In stark contrast, the Lewis basic sulfide catalyst could promote the electrophilic bromolactonization and yield the Markovnikov product exclusively.

CuX2-mediated oxybromination/aminochlorination of unsaturated amides: Synthesis of iminolactones and lactams

We report herein a CuX2-mediated halocyclization of γ,δ-unsaturated amides for the synthesis of functionalized iminolactones and lactams respectively under mild reaction conditions. Mechanism studies indicated that N-attack cyclization was via a radical route while oxycyclization was via a nucleophilic attack on the activated CC bond.

Enantioselective synthesis of tetrahydrofuran derivatives by sequential henry reaction and iodocyclization of γ,δ-unsaturated alcohols

A sequential one-pot Cu-catalyzed asymmetric Henry reaction and iodocyclization is disclosed. The transformation provides efficient access to biologically and synthetically useful 2,2,5-trisubstituted tetrahydrofuran derivatives. The combination of Cu(OAc)2·H2O with a novel chiral sulfoxide-Schiff base hybrid ligand under mild reaction conditions tolerates a wide range of 4-substituted γ,δ-unsaturated aldehydes, and the subsequent iodocyclization furnishes the corresponding products in generally high yields with excellent enantioselectivities. The products can be easily converted into amines with excellent diastereo- and enantioselectivities.

Asymmetric iodolactonization utilizing chiral squaramides

Asymmetric iodolactonization of γ- and δ-unsaturated carboxylic acids has been explored in the presence of six different chiral organocatalysts 5-8. The catalyst 6b was found to facilitate the cyclization of 5-arylhex-5-enoic acids 1 to the corresponding

Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts

A facile and efficient enantioselective bromoaminocyclization of unsaturated sulfonamides has been developed using an amino-thiocarbamate catalyst. A range of enantioenriched pyrrolidines were prepared with up to 99% yield and 99% ee. The corresponding lactams could be obtained through oxidation of the pyrrolidines.

A peptide bromoiodinane approach for asymmetric bromolactonization

A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology.