223243-86-5

Upstream product

• 141-82-2 malonic acid 
• 34713-70-7 2-Phenylpropanal 
• 6051-52-1 2-phenylbut-3-en-2-ol 
• 201230-82-2 carbon monoxide 
• 64-18-6 formic acid 
• 98-86-2 acetophenone 
• 2085-88-3 2-methyl-2-phenyloxirane 
• 51114-94-4 (2-carboxyethyl)triphenylphosphonium bromide 

Downstream Products

• 87567-66-6 ethyl (E)-4-phenyl-3-pentenoate 
• 119271-86-2 (Z)-4-phenylpent-3-enoic acid 
• 16433-43-5 (R)-4-phenylpentanoic acid 
• 1548512-98-6 C₁₁H₁₁BrO₂ 
• 52264-92-3 (-)-(S)-5-methyl-5-phenylfuran-2(5H)-one 
• 52264-92-3 (+)-(R)-5-methyl-5-phenylfuran-2(5H)-one 
• 6049-50-9 4-Oxo-3-phenylpentanoic acid 
• 53774-21-3 5-methyl-5-phenyl-2,5-dihydrofuran-2-one 

Relevant academic research and scientific papers

Palladium-Catalyzed Low Pressure Carbonylation of Allylic Alcohols by Catalytic Anhydride Activation

A direct carbonylation of allylic alcohols has been realized for the first time with high catalyst activity at low pressure of CO (10 bar). The procedure is described in detail for the carbonylation of E-nerolidol, an important step in a new BASF-route to (?)-ambrox. Key to high activities in the allylic alcohol carbonylation is the finding that catalytic amounts of carboxylic anhydride activate the substrate and are constantly regenerated with carbon monoxide under the reaction conditions. The identified reaction conditions are transferrable to other substrates as well.

A Novel Method for the Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride

A facile chlorolactonization of alkenoic acids by treatment with diphenyl sulfoxide/oxalyl chloride has been developed. The reaction can generate various chlorolactones in moderate to good yields, wherein the chlorodiphenylsufonium salt derived from diphenyl sulfoxide/oxalyl chloride serves as the source of Cl +.

Stereoselective Ring-Opening of gem-Difluorocyclopropanes: An Entry to Stereo-defined (E,E)- and (E,Z)-Conjugated Fluorodienes

The ring-opening of gem-difluorocyclopropyl acetaldehydes producing selectively (E,E)- and (E,Z)-conjugated fluorodienals is described. Two stereo-divergent methods are presented to access both stereoisomers from a common precursor, in high yield and selectivity. The mechanistic aspect of these transformations is discussed.

Efficient Pd-Catalyzed Regio- and Stereoselective Carboxylation of Allylic Alcohols with Formic Acid

Formic acid is efficiently used as a C1 source to directly carboxylate allylic alcohols in the presence of a low loading of palladium catalyst and acetic anhydride as additive to afford β,γ-unsaturated carboxylic acids with excellent chemo-, regio-, and stereoselectivity. The reaction proceeds through a carbonylation process with in situ-generated carbon monoxide under mild conditions, avoiding the use of high-pressure gaseous CO. A bisphosphine ligand with a large bite angle (4,5-bis{diphenylphosphino}-9,9-dimethylxanthene, Xantphos) was found to be uniquely effective for this transformation. The regio- and stereoconvergence of this reaction is ascribed to the thermodynamically favored isomerization of the allylic electrophile in the presence of the palladium catalyst.

Direct palladium-catalyzed carbonylative transformation of allylic alcohols and related derivatives

A direct, palladium-catalyzed, carbonylative transformation of allylic alcohols for the synthesis of β,γ-unsaturated carboxylic acids has been developed. With formic acid as the CO source, various allylic alcohols were conveniently transformed into the corresponding β,γ-unsaturated carboxylic acids with excellent linear and (E)-selectivity. The reaction was performed under mild conditions; toxic CO gas manipulation and high-pressure equipment were avoided in this procedure.

BETA-TETRAZOLYL-PROPIONIC ACIDS AS METALLO-BETA-LACTAMASE INHIBITORS

The present invention relates to compounds of formula I that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.

Synthesis of chiral butenolides using amino-thiocarbamate-catalyzed asymmetric bromolactonization

The asymmetric cyclization of 4,4-disubstituted 3-butenoic acids is studied. Amino-thiocarbamates are used as the catalysts and N-bromosuccinimide is used as the stoichiometric halogen source. The resulting γ-butanolide products are readily converted into the corresponding γ-butenolides (up to 58% ee) derivatives in one-pot.

Tandem hydroboration/reduction of trisubstituted β,γ-unsaturated esters for the asymmetric synthesis of chiral 1,3-diols

Treatment of a range of trisubstituted β,γ-unsaturated esters with 2 equiv of (-)-monoisopinocampheylborane results in hydroboration of their alkene functionalities and reduction of their ester groups to afford chiral 1,3-diols containing two new vicinal

Enantioselective iridium-catalyzed hydrogenation of β,γ- unsaturated carboxylic acids: An efficient approach to chiral 4-alkyl-4-aryl butanoic acids

Chiral acids: A highly enantioselective iridium-catalyzed hydrogenation of β,γ-unsaturated carboxylic acids is developed for the preparation of chiral 4-alkyl-4-aryl butanoic acids (see scheme). Copyright

Catalytic addition-elimination reactions towards butenolides

A wide range of selenium-containing reagents are known to undergo addition - elimination reactions under different reaction conditions. We report on selenium electrophiles, which are regenerated under the reaction conditions employed, and therefore only catalytic amounts of these reagents are necessary.