5693-99-2

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 21915-53-7 2,3-epoxy-3-phenyl-1-propanol 
• 104-54-1 3-Phenylpropenol 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 99773-64-5 (1S,2R)-2-Bromo-1-hydroxy-4-methyl-1-phenyl-4-trimethylsilanyloxy-pentan-3-one 
• 21915-53-7 cis-2,3-epoxy-3-phenyl-1-propanol 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 99773-42-9 2-Hydroxy-2-methyl-1-((2S,3S)-3-phenyl-oxiranyl)-propan-1-one 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104-55-2 3-phenyl-propenal 
• 21915-53-7 (2R,3S)-(3-phenyloxiran-2-yl)methanol 
• 99773-42-9 2-Hydroxy-2-methyl-1-((2S,3R)-3-phenyl-oxiranyl)-propan-1-one 
• 76777-60-1 5-Hydroxy-5-phenyl-2-<(trimethylsilyl)oxy>-2-methyl-3-pentanone 
• 63677-96-3 (E)-2-hydroxy-2-methyl-5-phenylpent-4-en-3-one 

Downstream Products

• 79750-54-2 5-(3-Phenyl-2-oxiranyl)-2(Z),4(Z)-pentadiennitril 
• 79750-55-3 2-Methyl-5-(3-phenyl-2-oxiranyl)-2(E),4(Z)-pentadiensaeure-methylester 
• 79750-55-3 2-Methyl-5-(3-phenyl-2-oxiranyl)-2(E),4(E)-pentadiensaeure-methylester 
• 74026-41-8 2-<4-(4-Methoxyphenyl)-1(Z),3(E)-butadienyl>-3-phenyloxiran 
• 74026-41-8 2-<4-(4-Methoxyphenyl)-1(E),3(E)-butadienyl>-3-phenyloxiran 
• 74026-42-9 2-<4-(4-Nitrophenyl)-1(Z),3(E)-butadienyl>-3-phenyloxiran 
• 74026-42-9 2-<4-(4-Nitrophenyl)-1(E),3(E)-butadienyl>-3-phenyloxiran 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 40641-81-4 trans-2,3-epoxy-3-phenylpropan-1-ol 
• 53422-64-3 epoxy-3,4 phenyl-4 butyne-1 (trans) 

Relevant academic research and scientific papers

Borylation and rearrangement of alkynyloxiranes: A stereospecific route to substituted α-enynes

1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes.

Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates

The reaction of epoxy aldehydes with tetraethyl methylenediphosphonate gave γ,δ-epoxy vinyl phosphonates. The palladium-catalyzed addition of primary alcohols gave the monoprotected diols as single diastereoisomers. The trans- and cis-epoxides lead to opp

Highly Regio- and Stereodivergent Access to 1,2-Amino Alcohols or 1,4-Fluoro Alcohols by NHC-Catalyzed Ring Opening of Epoxy enals

Described is an unprecedented NHC-catalyzed (NHC=N-heterocyclic carbene), stereoselective ring opening of epoxy and cyclopropyl enals to deliver valuable compounds bearing multiple stereocenters. A straightforward three-step procedure involving two catalytic enantioselective transformations has been developed and leads to a regio- and stereodivergent synthesis of either 1,2-amino alcohols/diamines or 1,4-fluoro alcohols with excellent diastereo- and enantiopurity.

Nanosheet-enhanced efficiency in amine-catalyzed asymmetric epoxidation of Α, Β-unsaturated aldehydes via host-guest synergy

Amine-catalyzed asymmetric epoxidation of α, β-unsaturated aldehydes has been promoted by attaching the nanosheets of layered double hydroxides (LDHs), a natural and/or synthetic anionic layered compound. 76% of epoxide yield and 93% ee of major diastereomer have been afforded in the asymmetric epoxidation of cinnamaldehyde. The amine sites employed here are the amino group in α-amino acid anion intercalated in the interlayer space of LDHs. The nanosheets of LDHs have been revealed to play key role in the enhancement of catalytic activity by affording the desired basicity and the boost of enantioselectivity by serving as the rigid substituent of amino acids. The hydrophobic interlayer microenvironment and ordered arrangement of intercalated amino acid anions additionally contribute to the catalytic efficacy. Stronger interlayer hydrophobicity favors the conversion and epoxide yield and better arrangement of interlayer anions favors the ee.

Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams

cis-3-Acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones were prepared through a Staudinger [2+2]-cyclocondensation between acetoxyketene and the appropriate epoxyimines in a highly diastereoselective way. Subsequent potassium carbonate-mediated acetate hydrolysis, followed by intramolecular ring closure through epoxide ring opening, afforded stereodefined 3-aryl-4-hydroxy-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones as a novel class of C-fused bicyclic β-lactams. Selective benzylic oxidation of bicyclic N-(4-methoxybenzyl)-β-lactams with potassium persulfate and potassium dihydrogen phosphate provided the corresponding N-aroyl derivatives as interesting leads for further β-lactamase inhibitor development.

Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst

The asymmetric epoxidation of α,β-unsaturated aldehydes, catalyzed by a spiro-pyrrolidine (SPD)-derived organocatalyst, has been accomplished with good diastereoselectivities (up to dr >20:1) and with high to excellent enantioselectivities (up to 99% ee).

Highly efficient asymmetric synthesis of α,β-epoxy esters via one-pot organocatalytic epoxidation and oxidative esterification

Highly enantioselective synthesis of α,β-epoxy esters was achieved via one-pot organocatalytic epoxidation and consequent oxidative esterification. Excellent enantioselectivities (up to 99% ee) and good yields were obtained for a variety of α,β-epoxy esters. The method was readily scaled. Furthermore the product was applied towards the synthesis of (-)-clausenamide with excellent enantioselectivities (>99% ee).

Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions

An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, 'green' fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses. The Royal Society of Chemistry 2012.

A new, simple, and mild azidolysis of vinylepoxides

A new, simple, and mild regio-and stereocontrolled azidolysis of vinylepoxides with TMSN3/BF3 system is reported. The method appears of general value and works very well particularly in the presence of electron-poor olefins, regardless of the size of substituents on the heterocyclic ring.