1360652-03-4

Upstream product

• 131119-24-9 3-Benzylidene-1,5-dioxa-spiro[5.5]undecane-2,4-dione 
• 135-19-3 β-naphthol 
• 4352-89-0 3H-benzo[f]chromen-3-one 
• 98-80-6 phenylboronic acid 
• 5690-03-9 splitomicin 
• 104-55-2 3-phenyl-propenal 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 2579-22-8 Phenylpropargyl aldehyde 

Relevant academic research and scientific papers

Palladium Catalyzed Enantioselective Hayashi-Miyaura Reaction for Pharmaceutically Important 4-Aryl-3,4-dihydrocoumarins

The first palladium-catalyzed asymmetric addition of arylboronic acids to coumarins was successfully established, providing a straightforward asymmetric approach to achieving pharmaceutically important 4-aryl-3,4-dihydrocoumarins. This methodology features easily accessible and bench-stable ligands, a wide substrate scope, mild conditions, and accommodation of electron-withdrawing arylboronic acids.

Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond

A highly efficient enantioselective [1,3] O-to-C rearrangement of racemic vinyl ethers that operates under mild conditions was developed. This method with chiral ferrous complex catalyst provided an efficient access to a wide range of chromanols with high yields and excellent enantioselectivities. In addition, an important urological drug (R)-tolterodine and others were easily obtained after simple transformations.

Enantioselective Arylation of Benzylic C?H Bonds by Copper-Catalyzed Radical Relay

A novel enantioselective copper-catalyzed arylation of benzylic C?H bonds, using alkylarenes as a limiting reagent, has been developed. A chiral bisoxazoline ligand bearing an acetate ester moiety plays a key role in both the reactivity and enantioselectivity of the reaction. The reaction provides efficient access to various chiral 1,1-diarylalkanes in good yields with good to excellent enantioselectivities, and displays excellent functional-group tolerance.

With 3, 4 - ISO-quinoline skeleton of chiral nitrogen heterocyclic carbene precursor salt, methods of synthesis and use

The invention provides a chiral N-heterocyclic carbene precursor salt with a 3,4-dihydroisoquinoline skeleton, a synthetic method and application. The precursor salt has the structural formula as shown in the specification. The precursor salt can be prepa

Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine

A series of chiral triazolium salts have been synthesized from methyl l-phenylalaninate hydrochloride. The NHCs derived from this class of novel triazolium salts were found to be highly efficient catalysts in the annulation reaction of enals and 2-naphthols. These reactions proceeded with high chemoselectivity and wide substrate scope affording enantioenriched β-arylsplitomicins in good yields with up to 96% ee. This journal is

Enantioselective N-Heterocyclic Carbene-Catalyzed Annulations of 2-Bromoenals with 1,3-Dicarbonyl Compounds and Enamines via Chiral α,β-Unsaturated Acylazoliums

The N-heterocyclic carbene (NHC)-catalyzed generation of chiral α,β-unsaturated acylazoliums from 2-bromoenals followed by their interception with 1,3-dicarbonyl compounds or enamines, the formal [3+3] annulation reaction, is reported. The reaction results in the enantioselective synthesis of synthetically and medicinally important dihydropyranones and dihydropyridinones, and tolerates a wide range of functional groups. It is noteworthy that the reaction takes place under mild reaction conditions utilizing relatively low catalyst loadings. In addition, based on DFT calculations, a mechanistic scenario involving the attack of the nucleophile from below the plane of the α,β-unsaturated acylazoliums, and the mode of enantioinduction is presented. Copyright

Organocatalytic synthesis of enantioenriched β-arylsplitomicins

By employing a chiral bifunctional thiourea-tertiary amine as catalyst, domino Michael-type Friedel-Crafts alkylation/cyclization of -naphthols with akylidene Meldrum's acids was realized. The reactions afforded various enantioenriched -arylsplitomicins with good yields (up to 99%) in moderate enantioselectivities (up to 79%). Georg Thieme Verlag Stuttgart · New York.

An enantioselective claisen rearrangement catalyzed by N-heterocyclic carbenes

In the presence of a chiral azolium salt (10 mol %), enols and ynals undergo a highly enantioselective annulation reaction to form enantiomerically enriched dihydropyranones via an N-heterocyclic carbene catalyzed variant of the Claisen rearrangement. Unlike other azolium-catalyzed reactions, this process requires no added base to generate the putative NHC-catalyst, and our investigations demonstrate that the counterion of the azolium salt plays a key role in the formation of the catalytically active species. Detailed kinetic studies eliminate a potential 1,4-addition as the mechanistic pathway; the observed rate law and activation parameters are consistent with a Claisen rearrangement as the rate-limiting step. This catalytic system was applied to the synthesis of enantioenriched kojic acid derivatives, a reaction of demonstrated synthetic utility for which other methods for catalytic enantioselective Claisen rearrangements have not provided a satisfactory solution.