136378-00-2

Upstream product

• 123-38-6 propionaldehyde 
• 78-94-4 methyl vinyl ketone 

Relevant academic research and scientific papers

The first air-stable and efficient nucleophilic trialkylphosphine organocatalyst for the Baylis-Hillman reaction

1,3,5,-Triaza-7-phosphaadamantane (PTA) is first reported to be a convenient and efficient nucleophilic trialkylphosphine organocatalyst for the Baylis-Hillman reaction. Thus, under the mediation of 15-20 mol % of PTA and practical conditions, both aromat

A selective synthesis of α-methylene-β-hydroxyalkanones catalyzed by RuH2(PPh3)4

The RuH2(PPh3)4-catalyzed coupling of vinylketones with aldehydes accomplishes the selective synthesis of α-methylene-β-hydroxyalkanones under neutral conditions.A plausible pathway involving possible intermediacy of a ruthenium enolate is proposed.

Enantioselective approaches to rhodium catalysed aldol-type reactions

Homochiral catalysts, [Rh(norbornadiene)-(homochiral diphosphine)]+ X-/H2, were tested to assess possible enantiocontrol in the aldol-type coupling of activated vinyl components with aldehydes. A related approach, via in situ rhodium silyl enolates, was also investigated.

Ultrasound in Baylis-Hillman reactions with aliphatic and aromatic aldehydes: Scope and limitations

The utilization of ultrasound radiation in the Baylis-Hillman reaction with several aldehydes (aromatics and aliphatics) and different α,β-unsaturated reactants is described. For all aldehydes tested, the utilization of ultrasound sources augmented the reaction rate and the chemical yields. The use of ultrasound with two different catalysts (tri-n-butylphosphine and 1,4-diazabicyclo[2.2.2]octane [DABCO]) was also investigated. It was clearly demonstrated that DABCO is much more effective for catalyzing a Baylis-Hillman reaction under the influence of ultrasound than is tri-n-butylphosphine. No effect on reaction rate was observed when the concentration of DABCO was increased.

Sulfide-BF3·OEt2 mediated Baylis-Hillman reactions

A sulfide-BF3·OEt2 mediated Baylis-Hillman reaction has been developed in which the sulfide acts via attack onto the activated alkene. The use of a chiral sulfide gives rise to Baylis-Hillman adducts with up to 53% ee.

Lithium perchlorate-accelerated Baylis-Hillman reactions

The coupling of α, β-unsaturated carbonyl compounds with aldehydes (the Baylis-Hillman reaction) was accelerated in the presence of a catalytic amount of 1,4-diazabicyclo[2,2,2]octane (DABCO) and lithium perchlorate in ether. A preliminary kinetic study r

Reaction of a cyclic oxosulfonium ylide with acetates of the Baylis-Hillman adducts: Tandem Michael - Intramolecular Corey-Chaykovsky reactions

(equation presented) The reaction of the five-membered cyclic oxosulfonium ylide 2 with α-methylene-β-acetoxy ketones in the presence of two equimolar amounts of base afforded the cycloheptene oxide derivatives with stereoselectivity in 19-74% yield via a

Stereoselective epoxidation of hydroxyenones. The synthesis of the sidechain of clerocidin

The sidechains of clerocidin 1 and terpentecin 2 contain a unique chiral assembly [C5H5O4]. Models for the stereospecific synthesis of this structural feature are reported.

Rhodium(I)- or ruthenium(II)-catalyzed direct coupling of vinyl ketones with aldehydes and the subsequent reduction to give aldol derivatives anti-selectively

A vinyl ketone reacts with an aldehyde to give an α-methylene-β-hydroxyalkanone with the concomitant formation of the vinyl ketone dimer in the presence of catalytic amount of RhH(PPh3)4 or RuH2(PPh3)4 under almost neutral conditions.The selectivity of th

Nucleophile-Catalysed Additions of Aldehydes and Ketones to Acrylic Compounds: The Effectiveness of High Pressures

The preparation of a wide range of compounds of general type: CH2=C(Z)-CR1R2OH (Z = CN, COOR, CHO,; R1,R2 = H, alkyl, aryl) from the reaction of CH2=CHZ with aldehydes and ketones, is effectively catalysed by tertiary amines especially DABCO.Rates are found to be very strongly accelerated by high pressures (2-10 kbar) which alone permits the additions of ketones or of crotonic acid derivatives to take place.In the absence of carbonyl acceptors novel oligomers of acrylic compounds form.