82864-15-1

Upstream product

• 591-51-5 phenyllithium 
• 5416-70-6 2-methoxychalcone 
• 98-86-2 acetophenone 
• 135-02-4 ortho-anisaldehyde 
• 532-27-4 1-chloroacetophenone 
• 22965-99-7 (E)-3-(2-methoxylphenyl)-1-phenylprop-2-en-1-one 

Relevant academic research and scientific papers

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe3)2]3with chiral TADDOL ligands

The catalytic asymmetric epoxidation of α,β-unsaturated ketones by tert-butylhydroperoxide (TBHP) has been well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = La(1), Nd(2), Sm(3), Y(4), Yb(5)) with chiral TADDOL ligands. It was found that

Synthesis of xylal- and arabinal-based crown ethers and their application as asymmetric phase transfer catalysts

New xylal- and arabinal-based monoaza-15-crown-5 ethers were synthesized starting from l- and d-xylose, and l- and d-arabinose, respectively. These monosaccharide-based chiral macrocycles were tested as phase transfer catalysts in a few asymmetric reactions. The xylal-based crown compounds proved to be efficient catalysts in a few liquid-liquid phase reactions. The epoxidation of trans-chalcone and the Darzens condensation of α-chloroacetophenone with benzaldehyde took place with complete diastereoselectivity and up to 77% ee and 58% ee, respectively. It was found that the substituents in the aromatic ring of the chalcone and the α-chloroacetophenone had an influence on the enantioselectivity. The highest ee values were obtained in the epoxidation of 4-chlorochalcone (81% ee) and in the reaction of a 2-naphthyl analogue (96% ee), while in the Darzens condensation of 4-phenyl-α-chloroacetophenone with benzaldehyde, a maximum ee of 91% was detected. The configuration of the monosaccharide unit in the crown ring influenced the absolute configuration of the epoxyketones synthesized.

Lanthanide complexes combined with chiral salen ligands: Application in the enantioselective epoxidation reaction of α,β-unsaturated ketones

Readily available lanthanide amides Ln[N(SiMe3)2]3 (Ln = Nd (1), Sm (2), Eu (3), Yb (4), La (5)), combined with chiral salen ligands H2La ((S,S)-N,N′-di-(3,5-disubstituted-salicylidene)-1,2-cyclohexan

One-pot production of chiral α,β-epoxy ketones from benzaldehydes and acetophenones by recyclable poly(amino acid) catalysis

An efficient one-pot, two-step process was disclosed for production of chiral α,β-epoxy ketones from benzaldehydes and acetophenones catalyzed by imidazolium-modified poly(l-leucine). Two effective reaction systems with complementary high enantioselectivities (up to 98% ee) or satisfactory yields (up to 89%) have been developed. Importantly, the poly(amino acid) catalyst can be easily recovered and recycled for ten times without losing its catalytic efficiency in terms of both enantioselectivity and yield.

Asymmetric epoxidation of substituted chalcones and chalcone analogues catalyzed by α-d-glucose- and α-d-mannose-based crown ethers

The chiral monoaza-15-crown-5 lariat ethers annellated to methyl-4,6-O-benzylidene-α-d-glucopyranoside-1 or mannopyranoside 2 have been applied as phase-transfer catalysts in the epoxidation of substituted chalcones and chalcone analogues with tert-butylhydroperoxide resulting in significant asymmetric induction. It was found that the position of the substituents in the aromatic ring of the chalcone had an influence both on the chemical yields and enantiomeric excesses. The lowest enantioselectivities (62-83% ee) were found in the case of ortho-substituted model compounds. The highest ee values (ee of 83-97%) were obtained in the case of para-substituted models. From among the chalcone analogues, the maximum ee (90-92%) was detected for the model compound having α-tert-butyl- and β-aryl groups. Using glucose-based crown ether 1, formation of the (-)-enantiomer was preferred, while applying mannose-based 2 as the catalyst, the (+)-enantiomer was in excess.

Imidazolium-modified poly(l-leucine) catalyst: an efficient and recoverable catalyst for Juliá-Colonna reactions

A novel, easily recyclable imidazolium-modified poly(amino acid) catalyst was prepared. This catalyst exhibits high activity for the asymmetric epoxidation of α,β-unsaturated ketones without any pre-activation. The enantioselectivity was up to 99% ee for

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by silica-grafted poly-(L)-leucine catalysts

A practical procedure has been developed for grafting poly(amino acid) on silica gel as an efficient and recoverable catalyst in the Juliá-Colonna asymmetric epoxidation with high enantioselectivities. Separation and recovery of the catalyst of poly(amino

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by chiral ytterbium complexes

Several derivatives of (S)-(-)-BINOL ligands with 6,6′-substitutents were synthesized and applied as chiral ligands in the Yb(O-i-Pr)3-catalyzed asymmetric epoxidation of α,β-unsaturated ketones. Superior results were obtained with 6,6′-diphenyl-BINOL, exemplified in the asymmetric epoxidation of (E)-1,3-diphenylprop-2-en-1-one in 91% yield and up to 97% ee.

A rapid, simple route to homochiral α,β-epoxyketones

Substituted E- or Z-acrylylamides derived from a homochiral amine such as (R,R)-2,5-dimethylpyrrolidine or (S,S)-bis(2-phenylethyl)amine are readily epoxidised with complete stereocontrol with t-BuO2Li to give two readily separated, enantiomerically pure diastereomeric epoxides. The easily separated epoxides are efficiently converted into α,β-epoxyketones by the action of organolithiums with 92->99% ee.