784143-65-3

Upstream product

• 1072-72-6 Tetrahydrothiopyran-4-one 
• 100-52-7 benzaldehyde 

Downstream Products

• 804519-85-5 (3R,4R)-3-((R)-Hydroxy-phenyl-methyl)-tetrahydro-thiopyran-4-ol 
• 153668-22-5 erythro-1-hydroxy-2-methyl-1-phenyl-3-pentanone 
• 55848-19-6 1-Hydroxy-2-methyl-1-phenyl-pentan-3-one 

Relevant academic research and scientific papers

Chiral picolylamines for Michael and aldol reactions: Probing substrate boundaries

Here we report on inroads concerning increased substrate breadth via the picolylamine organocatalyst template, a vicinal chiral diamine based on a pyridine-primary amine motif. The addition of cyclohexanone to β-nitrostyrene has many catalyst solutions, b

Chiral picolylamines for Michael and aldol reactions: Probing substrate boundaries

Here we report on inroads concerning increased substrate breadth via the picolylamine organocatalyst template, a vicinal chiral diamine based on a pyridine-primary amine motif. The addition of cyclohexanone to β-nitrostyrene has many catalyst solutions, b

Organocatalytic enantioselective direct aldol reaction in aqueous media catalyzed by a bifunctional diamine catalyst

Organocatalytic direct asymmetric anti-aldol reaction was developed in aqueous medium using a BINOL-derived diamine/protic acid bifunctional catalyst. The catalytic protocol could offer the opportunity to access anti-aldol products with high level of enan

Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions

A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize β-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer.

Enantioselective direct aldol reactions of achiral ketones with racemic enolizable α-substituted aldehydes: Scope and limitations

Aldol reactions of racemic enolizable dioxolan-protected α-substituted-β-ketoaldehydes with representative achiral ketones catalyzed by proline or 5-(2-pyrrolidine-2-yl)-1H-tetrazole in wet DMSO proceed with dynamic kinetic resolution (or via DYKAT with an α-substituted- β-alkoxyaldehyde) to give adducts with high dr and ee. Georg Thieme Verlag Stuttgart.

Highly efficient small organic molecules for enantioselective direct aldol reaction in organic and aqueous media

(Chemical Equation Presented) A series of highly efficient organocatalysts have been derived from naturally available amino acids for carrying out enantioselective direct aldol reaction in both organic and aqueous medium. The aldol products were obtained in high diastereoselectivities (up to 99:1) and enantioselectivities (up to >99% ee) for a broader range of substrates using 1 mol % of a catalyst. The results demonstrate that the structural features of organocatalysts play a crucial role in obtaining high optical purity of aldol adducts in an aqueous medium. Further, the role of water in increasing the rate and enantioselectivity of the reaction has been illustrated. Moreover, the aldol products have been employed in the synthesis of chiral amino alcohols which act as useful intermediates for building up complex natural products.

Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst

Chiral phosphine oxide successfully catalyzed the direct aldol-type reactions of cyclohexanone derivatives and benzaldehyde derivatives in high stereoselectivities. The reaction mechanism involves the in situ formation of trichlorosilyl enol ethers. The present reaction could be extended to the cross-aldol reactions between two aldehydes.

Primary amine-metal lewis acid bifunctional catalysts: the application to asymmetric direct aldol reactions

The first example of metal Lewis acid-primary amine bifunctional cooperative catalyst derived from primary amino acids was developed, and it was found to catalyze aldol reactions of cyclic ketones highly efficiently with very good to excellent stereoselec

Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions

4-Hydroxy-prolinamide alcohol with different noncoordination sites as a molecule showed excellent asymmetric catalytic activity in both the Michael reaction (up to 98% ee) and the direct aldol reaction (up to >99% ee), and the catalyzing reactions with hi

Synthesis of chiral organocatalysts derived from aziridines: Application in asymmetric aldol reaction

(Chemical Equation Presented) We report the synthesis of a new series of highly efficient chiral organocatalysts derived via the regio-and stereoselective ring opening of chiral aziridines with azide anions. The catalysts have proved to be very efficient