177314-50-0

Upstream product

• 3160-32-5 4-methyl-1-phenyl-1-penten-3-one 
• 3160-32-5 (1E)-4-methyl-1-phenylpent-1-en-3-one 
• 100-52-7 benzaldehyde 
• 563-80-4 3-methyl-butan-2-one 

Downstream Products

• 354576-53-7 (+)-(1S,2S,3R)-1-Chloro-4-methyl-1,3-diphenylpentane-2,3-diol 
• 354576-57-1 (-)-(1R,2S,3R)-1-Chloro-1,3-diphenyl-4-methylpentane-2,3-diol 
• 354576-51-5 (-)-(1S,2S,3R)-2,3-Epoxy-4-methyl-1,3-diphenyl-pentan-1-ol 
• 600173-55-5 (-)-(1S,2S,3S)-2,3-epoxy-4-methyl-1-phenyl-3-vinyl-1-pentanol 
• 602314-57-8 (4S,5R)-4-hydroxy-3-isopropyl-5-phenyl-4,5-dihydro-isoxazole 
• 354576-49-1 (+)-(1S,2R,3R)-1,2-Epoxy-1,3-diphenyl-4-methylpentan-3-ol 

Relevant academic research and scientific papers

A new procedure for the Julia-Colonna stereoselective epoxidation reaction under non-aqueous conditions: The development of a catalyst comprising polyamino acid on silica (PaaSiCat)

Polyleucine adsorbed onto silica provides a robust, readily-recycled, highly active catalyst for the asymmetric epoxidation of the α,β-unsaturated ketones 1, 2, and 3.

Asymmetric Epoxidation of Enones Promoted by Dinuclear Magnesium Catalyst

Asymmetric synthesis with cheaper and non-toxic alkaline earth metal catalysts is becoming an important and sustainable alternative to conventional catalytic methodologies mostly relying on precious metals. In spite of some sustainable methods for enantioselective epoxidation of enones, the development of a well-defined and efficient catalyst based on magnesium complexes for these reactions is still a challenging task. In this perspective, we present the application of chiral dinuclear magnesium complexes for asymmetric epoxidation of a broad range of electron-deficient enones. We demonstrate that the in situ generated magnesium-ProPhenol complex affords enantioenriched oxiranes in high yields and with excellent enantioselectivities (up to 99% ee). Our extensive study verifies the literature data in this area and provides a step forward to better understand the factors controlling the oxygenation process. Elaborated catalyst offers mild reaction conditions and a truly wide substrate scope. (Figure presented.).

Enantioselective epoxidation of α,β-unsaturated ketones catalyzed by stapled helical l-Leu-based peptides

Stapled helical l-leucine-based heptapeptides were synthesized and used as catalysts for the enantioselective epoxidation of α,β-unsaturated ketones. All N-terminal free stapled peptides were successfully used as chiral catalysts. Among them, the use of H-hS3,7hS-10 gave epoxide products with high enantioselectivities of up to 99% ee. Furthermore, the dominant conformations of the N-terminal protected stapled peptides R 3,7R-10 and hS3,7hS-10 were investigated by 1H NMR, IR, CD spectra, and X-ray crystallographic analysis. The peptide R3,7R-10 formed a right-handed (P) α-helix in solution and in the crystalline state, while hS 3,7hS-10 formed a right-handed (P) 310-helix in solution.

Stabilized α-helix-catalyzed enantioselective epoxidation of α,β-unsaturated ketones

(Equation Presented). Chiral cyclic α-amino acid containing oligopeptide catalyzed highly enantioselective epoxidation of α,β-unsaturated ketones and the α-helical secondary structure of the peptide catalyst were revealed by X-ray crystallographic analysis.

Enantioselective epoxidation of electrophilic olefins by using glycosyl hydroperoxides

Anomeric hydroperoxides derived from 3,4,6-tri-O-benzyl-galactose and glucose were used for enantioselective epoxidation of naphthoquinone (12), chalcone (13), (E)-1,2-dibenzoyl ethylene (14) and (E)-iso-butyryl-phenyl ethylene (15). In the presence of sodium hydroxide, the epoxidations showed exceptional high asymmetric induction. The exchange of sodium by a potassium ion resulted in a low asymmetric induction. These results pointed to the crucial role of the counterion and strongly suggested that coordination of the alkaline ion occurs in the transition state of the epoxidation process by both reagents, hydroperoxide and the olefin. Theoretical studies of the reaction mechanism at the DFT B3LYP/6-31G* level fitted very well with experimental results.

A route to the structure proposed for puetuberosanol and approaches to the natural products marshrin and phebalosin

Synthesis of the structure claimed for puetuberosanol 1 (using the Juliá-Colonna oxidation in a key step) showed that the natural product was a different material. The isomeric epoxy alcohols 16-18 can be discounted from the alternatives. An analogue 19 of marshrin 2 was prepared but the synthesis of the natural product was thwarted by failure of a Juliá-Colonna oxidation in the key step. The epoxy ketone 29 was prepared by Darzens condensation and was converted into (±)-phebalosin 3.

Stereocontrolled conversion of some optically active (4S,5R)-dihydroisoxazoles into acyclic 3-acetamido-1,2-diols

Optically active (4S,5R)-dihydroisoxazoles 5a-c (90-91% ee) have been prepared by reaction of the epoxyketones 4a-c with hydroxylamine. Reduction of compounds 5a and 5b using lithium aluminium hydride took place exclusively from the Re face to give (1R,2S,3S)-1,3-disubstituted-3-aminopropane-1,2-diols 6a and 6b. These amino-diols were characterised by N-acetylation and the stereochemical sense of the hydride reduction was confirmed by conversion of amides 7a and 7b into α-amino acid derivatives 10a and 10b.

Synthesis and reactions of some optically active epoxides formally derived from tertiary allylic alcohols

The epoxyketones 2, 3 and 7-9 reacted with Grignard reagents in a highly stereocontrolled manner to give the epoxyalcohols 20, 4-6 and 11-13 in high yields. The epoxyalcohol 12 underwent a Payne rearrangement on base treatment to give the isomer 15 while

A Class of C2 and Pseudo C2 Symmetric Ketone Catalysts for Asymmetric Epoxidation. Conformational Effect on Catalysis

A class of C2 and pseudo C2 symmetric ketones with one fused ring at each side of the carbonyl group have been prepared from quinic acid and found to be effective catalysts for the asymmetric epoxidation of a variety of olefins. Electron deficient olefins such as enones can be efficiently epoxidized. Encouragingly good enantioselectivity is also obtained for the epoxidation of styrenes. The studies show that the ketone conformation plays an important role in the reactivity and selectivity of the catalyst.

Water vs. desiccant. Improvement of Yb-BINOL complex catalyzed enantioselective epoxidation of enones

The Yb-BINOL-complex-catalyzed enantioselective epoxidation of α,β- unsaturated ketones (enones) was greatly improved by addition of a small amount of water (ca. 5 equiv to Yb). Optimized conditions and a plausible mechanism of the role of water and molec