890022-08-9

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 22822-85-1 ethyl sodiodiethylphosphonoacetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 105-36-2 ethyl bromoacetate 
• 73737-55-0 (E)-4-phenylbut-3-enal 

Downstream Products

• 58506-33-5 5-phenyl-trans,trans-2,4-pentadien-1-ol 
• 1552-94-9 (2Z,4E)-5-phenylpenta-2,4-dienoic acid 
• 192886-57-0 (4E)-5-phenylpenta-2,4-dien-1-ol 
• 137151-67-8 (S)-(E)-5-phenyl-1-(trimethylsilyl)-3-vinyl-4-penten-1-one 
• 137151-67-8 (E)-(R)-5-Phenyl-1-trimethylsilanyl-3-vinyl-pent-4-en-1-one 
• 137151-60-1 (2E,4E)-5-phenyl-2,4-pentadienyl 1-(trimethylsilyl)vinyl ether 
• 102106-95-6 (2Z,4E)-5-phenylpenta-2,4-diene-1-ol 

Relevant academic research and scientific papers

New solid-supported phosphonate reagents for the synthesis of Z-α,β-unsaturated esters

Novel solid-supported phosphonate reagents have been prepared and evaluated for the synthesis of α,β-unsaturated esters with a preference for the Z-alkene. The optimal reagent was a hybrid of both Still-Gennari and Ando reagents, and showed good to high yields and fair to good Z-selectivity for the conversion of both aliphatic and aromatic aldehydes.

Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole

A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.

One-pot Wittig reactions in water and in the presence of a surfactant

α,β-Unsaturated esters were synthesized in open atmosphere via mild and efficient one-pot Wittig reactions performed in both water and sodium dodecyl sulfate (SDS)-water solution. Georg Thieme Verlag Stuttgart.

Two variations of solvent-reduced wittig olefination reactions - Comparison of solventless wittig reactions to wittig reactions under ultrasonication with minimal work-up

Stabilized and semi-stabilized phosphoranes can be subjected to solventless Wittig reactions with carbaldehydes. Simple heating of a mixture of added components at 100°C in an electric oven gives the corresponding olefins in good yield. Alternatively, the Wittig reactions can be carried out in a biphasic medium under ultrasonication. In this case, the Wittig products can be isolated by simple evaporation of the organic phase without additional work-up.

Methylenation of aldehydes: Transition metal catalyzed formation of salt-free phosphorus ylides

A variety of terminal alkenes are produced in excellent yields by the rhodium(I)-catalyzed methylenation of aldehydes using TMSCHN2 and PPh3 [Eq. (1)]. These mild reaction conditions allowed the conversion of enolizable substrates and the chemoselective methylenation of aldehydes over ketones. TMS = trimethylsilyl.

A new procedure for Horner-Wadsworth-Emmons olefination of carbonyl compounds

Aldehydes undergo an efficient E-stereoselective Horner-Wadsworth-Emmons olefination by generation of phosphonate carbanion with lithium hydroxide. The reaction proceeds satisfactorily with linear, cyclic, polifunctional ketones in the presence of activated zeolites and by the slow addition of the base.

Enantioselective activation of ethers by chiral organoaluminum reagents: Application to asymmetric Claisen rearrangement

The asymmetric Claisen rearrangement of allyl vinyl ethers has been effected with a chiral organoaluminum reagent, (R)-1 or (S)-1 as an example of the enantioselectie activation of ether substrates. This method provides a facile asymmetric synthesis of various acylsilanes and acylgermanes with high optical purity. Among various trialkylsilyl substituents of chiral organoaluminum reagent 1, use of the more bulky t-butyldiphenylsilyl group exhibits the highest enantioselectivity. The conformational analysis of two possible chairlike transition-state structures of an allyl vinyl ether substrate reveals that a chiral organoaluminum reagent 1 can discriminate between these two conformations only by a difference in the orientation of α-methylene groups of ethers.

DISSYMETRATION DE LA MOLECULE DU GLYOXAL 1-SYNTHESE ET REACTIVITE DE L'ACETOXY-1 TRIETHOXY-1,2,2 ETHANE

Acetoxy-1 triethoxy-1,2,2 ethane, a dissymetric derivative of glyoxal, is prepared and reacted with various bases and nucleophiles, as amines, cyanotrimethylsilane, organometallic and WITTIG reagents.Various acetals are obtained, leading to α-fonctionalized aldehydes.