36884-75-0

Upstream product

• 13159-16-5 (E)-5-phenyl-4-penten-1-ol 
• 80816-23-5 (E)-3-phenyl-3-vinyloxyprop-1-ene 
• 107-18-6 allyl alcohol 
• 536-74-3 phenylacetylene 
• 201230-82-2 carbon monoxide 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 1198-34-1 2-Phenylcyclopentanone 
• 14371-10-9 (E)-3-phenylpropenal 
• 72651-96-8 (E)-2,2-dimethyl-5-(3-phenylallyl)-1,3-dioxane-4,6-dione 
• 22768-07-6 (E)-ethyl 5-phenylpent-4-enoate 
• 129454-82-6 2-((E)-5-phenylpent-4-enyloxy)tetrahydro-2H-pyran 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 93845-04-6 ethyl 5-phenyl-4-pentenoate 

Downstream Products

• 129454-83-7 methyl 7-phenyl-hepta-2,6-dienoate 
• 145049-20-3 (E)-2,2-Difluoro-3-hydroxy-7-phenyl-hept-6-enoic acid ethyl ester 
• 73737-61-8 trans-5-phenyl-4-pentenal oxime 
• 182322-19-6 ((E)-3-Methoxy-7-phenyl-hept-6-en-1-ynyl)-trimethyl-silane 
• 146537-77-1 diethyl (E)-2-bromo-8-methoxy-12-phnyl-1,11-dodecadiene-6-yne-4,4-dicarboxylate 
• 145049-45-2 ((E)-6,6-Difluoro-7-iodo-5-methoxymethoxy-hept-1-enyl)-benzene 
• 145049-23-6 (E)-2,2-Difluoro-3-methoxymethoxy-7-phenyl-hept-6-enoic acid ethyl ester 
• 1204739-25-2 (E)-7-phenylhept-6-en-1-yn-3-ol 
• 1308888-03-0 (S,E)-3-(nitromethyl)-5-phenylpent-4-enal 
• 1308888-04-1 (S,E)-5-(4-methoxyphenyl)-3-(nitromethyl)pent-4-enal 
• 58927-89-2 (+/-)-(E)-6-phenylhex-5-en-2-ol 
• 33599-88-1 (E)-6-phenylhex-5-en-2-one 

Relevant academic research and scientific papers

Ruthenium-catalysed coupling of allyl alcohol with alkynes: A new route to γ,δ-unsaturated acetals and aldehydes

γ,δ-Unsaturated acetals and aldehydes have been obtained via a new ruthenium-catalysed coupling of allyl alcohol with alkynes. The branched isomer is regioselectively formed. Comparative studies of catalyst precursors have shown that (C5Me5)Ru(IV) derivatives favours the formation of acetals and that, with (C5Me5)Ru(II) moieties, the reaction can be carried out either in water or without solvent at room temperature.

Ruthenium Catalysed Synthesis of Unsaturated Acetals and Aldehydes via C-C Bond Coupling of Alkynes with Allyl Alcohol

Terminal alkynes and allyl alcohol are coupled, with carbon-carbon bond formation, in the presence of a RuIV(C5Me5) catalyst, to give γ,δ-unsaturated acetals and with 4> or preferentially to produce the branched γ,δ-unsaturated aldehydes.

Organocatalytic, Organic Oxidant Promoted, Enamine C?H Oxidation/Cyclopropanation Reaction

Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.).

Enantioselective Organocatalytic Enamine C?H Oxidation/Diels- Alder Reaction

α,β-unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single-electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels-Alder reaction. This enantioselective one-pot transformation represents the first example of saturated aldehydes being used in domino Diels-Alder reaction processes and demonstrates the power of this protocol for construction of stereo-defined chiral compounds and building blocks. (Figure presented.).

Enantio- A nd regioselective: Ene-reductions using F420H2-dependent enzymes

In the past decade it has become clear that many microbes harbor enzymes that employ an unusual flavin cofactor, the F420 deazaflavin cofactor. Herein we show that F420-dependent reductases (FDRs) can successfully perform enantio-, regio- A nd chemoselective ene-reductions. For the first time, we have demonstrated that F420H2-driven reductases can be used as biocatalysts for the reduction of α,β-unsaturated ketones and aldehydes with good conversions (>99%) and excellent regioselectivities and enantiomeric excesses (>99% ee). Noteworthily, FDRs typically display an opposite enantioselectivity when compared to the well established FMN-dependent Old Yellow Enzymes (OYEs).

Radical Isomerization and Cycloisomerization Initiated by H? Transfer

Under H2 pressure, CoII(dmgBF2)2L2 (L = H2O, THF) generates a low concentration of an H? donor. Transfer of the H? onto an olefin gives a radical that can either (1) transfer an H? back to the metal, generating an isomerized olefin, or (2) add intramolecularly to a double bond, generating a cyclized radical. Transfer of an H? back to the metal from the cyclized radical results in a cycloisomerization. Both outcomes are favored by the low concentration of the cobalt H? donor, whereas hydrogenation and cyclohydrogenation are more likely with other catalysts (when the concentration of the H? donor is high).

Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation

While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.

Aerobic oxidative coupling between carbon nucleophiles and allylic alcohols: A strategy to construct β-(hetero)aryl ketones and aldehydes through hydrogen migration

Wacker heck of a reaction: A highly efficient PdII-catalyzed intermolecular oxidative-coupling reaction is reported, inspired by the fundamental Heck and Wacker processes. The (hetero)aryl-PdX species, originating from C-H activation step or desulfonyl hydrazides, coupled with allylic alcohols by using oxygen as the sole oxidant (see scheme). Copyright

Enantioselective thiourea-catalyzed intramolecular cope-type hydroamination

Catalysis of Cope-type rearrangements of bis-homoallylic hydroxylamines is demonstrated using chiral thiourea derivatives. This formal intramolecular hydroamination reaction provides access to highly enantioenriched α-substituted pyrrolidine products and represents a complementary approach to metal-catalyzed methods.

Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols: Synthetic targets inspired by blepharocalyxin D

trans-2,8-Dioxabicyclodecanes were prepared in high yield with the creation of up to three stereocenters in a single pot by the acid-mediated reaction of γ,δ-unsaturated alcohols with aldehydes (see scheme, Bn=benzyl). This versatile reaction enables the stereoselective introduction of substituents at the C3, C4, C7, and C9 positions of the bicyclic framework. Copyright