147331-78-0

Upstream product

• 19202-21-2 1-trans-cinnamoylpyrrolidine 
• 100-42-5 styrene 
• 110-62-3 pentanal 
• 1312775-37-3 1-(tert-butylperoxy)-1-phenylheptan-3-one 
• 102-92-1 Cinnamoyl chloride 
• 20157-19-1 1-phenyl-1-hepten-3-ol 
• 104-55-2 3-phenyl-propenal 
• 246236-69-1 (E)-1-((2R,5R)-2,5-Dimethyl-pyrrolidin-1-yl)-3-phenyl-propenone 
• 109-72-8 n-butyllithium 
• 246236-71-5 ((2R,5R)-2,5-Dimethyl-pyrrolidin-1-yl)-((2R,3S)-3-phenyl-oxiranyl)-methanone 

Downstream Products

• 938043-99-3 1-phenylheptane-1,2,3-triol 

Relevant academic research and scientific papers

The Stereocontrolled Formation of 1,2,3-Triols by Yeast-mediated Transformation of α-Keto Epoxides

3-Phenyl-2,3-epoxy ketones are transformed using baker's yeast into the corresponding 1,2,3-triols as one pure diastereoisomer (S,S,S and R,R,R) formed by syn ring opening of the epoxide after first reduction of the carbonyl group; the reaction results in the epoxy-oxygen becoming the mid OH group of the triol, implicating enzyme attack at the C-3 in the ring-opening reaction.

Iron-catalyzed carbonylation-peroxidation of alkenes with aldehydes and hydroperoxides

A three-component reaction of alkenes, aldehydes, and hydroperoxides catalyzed by FeCl2 to β-peroxy ketones has been achieved. This three-component reaction can be also applied to the synthesis of α-carbonyl epoxides, through either a stepwise base-induced epoxidation of the separated β-peroxy ketone products or a one-pot process by simply adding base to the reaction mixture after the completion of the three-component reaction.

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.

A stereocontrolled approach to electrophilic epoxides

Lithium t-butyl hydroperoxide (easily generated by addition of an alkyl-lithium to anhydrous t-butyl hydroperoxide in THF solution) is a powerful reagent for the epoxidation of electrophilic alkenes at -20 to 0 °C under full stereocontrol. Thus αβ-unsaturated esters, sulphones, sulphoximines, and amides are readily epoxidised with complete regio- and stereo-specificity and with considerable chiroselectivity (20-100%) when appropriate chiral auxiliaries such as menthyl, 8-phenylmenthyl, or a camphor-sulphonamide derivative are used. Asymmetric αβ-unsaturated sulphoximines undergo epoxidation with 100% diastereoselectivity. The only exceptions to stereocontrol noted are heavily substituted maleate esters such as di-t-butyl maleate. The αβ-epoxy amides are shown to be valuable sources of the corresponding epoxy ketones by treatment with an organolithium, allowing a stereo- and chemoselective entry in high yield to these useful intermediates.