38860-42-3

Upstream product

• 133589-20-5 tri-n-butyl(cis-epoxystyryl)tin 
• 100-52-7 benzaldehyde 
• 62668-02-4 (E)-1,3-diphenyl-2-propen-1-ol 
• 133589-20-5 trans-1-phenyl-2-(tributylstannyl)epoxyethane 
• 5411-12-1 chalcone epoxide 
• 3262-89-3 triphenylboroxine 
• 14371-10-9 (E)-3-phenylpropenal 
• 557-20-0 diethylzinc 
• 4663-33-6 1,3-diphenyl-3-hydroxypropene 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 94-41-7 (Z)-chalcone 
• 536-74-3 phenylacetylene 
• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 
• 62839-70-7 (2Z)-1,3-diphenyl-2-propen-1-ol 

Downstream Products

• 5411-12-1 cis-1,3-Diphenyl-2,3-epoxypropan-1-one 
• 108638-32-0 1-Chloro-2,3-epoxy-1,3-diphenylpropane 
• 41049-36-9 1-hydroxy-1,3-diphenylacetone 
• 42052-51-7 3-hydroxy-1,3-diphenylpropan-1-one 
• 5411-12-1 (2S,3R)-phenyl(3-phenyloxiran-2-yl)methanone 
• 5411-12-1 trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one 
• 78043-55-7 (Z)-1-Phenyl-2-(phenylmethoxy)ethene 
• 69520-20-3 (E)-1-Phenyl-2-(phenylmethoxy)ethene 

Relevant academic research and scientific papers

Zinc-Mediated Efficient and Selective Reduction of Carbonyl Compounds

We herein describe for the first time that an optimized combination of Zn and NH4Cl can be used for the selective reduction of aldehydes and ketones to the corresponding alcohols. The aldehyde and keto groups are selectively reduced in the presence of azide, cyano, epoxy, ester, and carbon–carbon double-bond functional groups. A broad functional-group compatibility, chemoselective reduction of aldehydes in the presence of ketones, and selective reduction of isatins at the C3 carbonyl group are the highlights of the present method.

Synthesis of virtually enantiopure aminodiols with three adjacent stereogenic centers by epoxidation and ring-opening

A virtually complete enantioselective synthesis of 3-amino-1,2-diols with three consecutive stereocenters was accomplished by a sequential cascade of two kinetic resolutions, which features a Sharpless or Hafnium-catalyzed asymmetric epoxidation and a subsequent W-catalyzed aminolysis. Enantiopure products with up to >99.9% ee and >99.9:0.1 dr were obtained and could serve as potential building blocks for pharmaceutical or biological significant molecules.

Enantioselective one-pot catalytic synthesis of 4,5-epoxy-3-alkanols and 1-Phenyl-2,3-epoxy-1-alkanols from α,β-unsaturated aldehydes

Conformationally restricted perhydrobenzoxazines have been demonstrated to be good chiral ligands for one-pot asymmetric ethylation/epoxidation, and the unprecedented arylation/epoxidation of trisubstituted α,β-unsaturated aldehydes. The scope of the reaction has been studied and a wide set of substrates with allylic strain of different nature has been explored, obtaining good or total diastereoselectivities in all cases. The enantiocontrol was good or high for the ethylation/epoxidation reaction, whereas it remained at moderate or good levels for the arylation/epoxidation. The reaction is general for trisubstituted enals, and alkylic and aromatic substituents are tolerated at both the α- and β-position of the unsaturated aldehyde; however, disubstituted enals remain challenging substrates. When the one-pot and two-pot protocols were compared, no significant differences concerning the stereocontrol were found, so the advantages of the one-pot procedure are clear. Copyright

Indium-promoted chemo- and diastereoselective allylation of α,β-epoxy ketones with potassium allyltrifluoroborate

A practical method for the chemo- and diastereoselective allylation of α,β-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford α,β-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.

Poly(per)fluoroalkanesulfonyl fluoride promoted olefin epoxidation with 30% aqueous hydrogen peroxide

Epoxidation of various electron rich olefins with a novel oxidation system of poly(per)fluoroalkanesulfonyl fluoride/hydrogen peroxide/base is reported.

Asymmetric epoxidation via phase-transfer catalysis: Direct conversion of allylic alcohols into α,β-epoxyketones

Studies into the use of a chiral phase-transfer catalyst in conjunction with sodium hypochlorite to effect the enantio-selective formation of α,β-epoxyketones from allylic alcohols are described.

Applications of free and resin-bound novel (trifluoromethyl)dioxiranes

Recyclable resin-bound and other trifluoromethyl aryl ketones are efficient catalysts for oxone mediated epoxidations.

Chemo- and stereoselective reduction of α,β-epoxyketones with diisopropoxytitanium(III) tetrahydroborate

Reduction of α,β-epoxyketones with diisopropoxytitanium(III) tetrahydroborate in dichloromethane under mild conditions (-78°→20°C) provides anti- (or erythro-) α,β-epoxy alcohols in high yields with high degree of chemo- and stereoselectivity.

Novel Synthesis of syn-α,β-Epoxy Alcohols by Diastereoselective Carbonyl Reduction of α,β-Epoxy Ketones

A novel tin hydride reagent, Bu3SnH-Bu4NCN, reduced α,β-epoxy ketones to the corresponding syn-α,β-epoxy alcohols in high diastereoselectivities.