77565-69-6

Upstream product

• 69366-39-8 dilithiated acetic acid 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 18365-23-6 methyl 2-(tributylstannyl)acetate 
• 67-56-1 methanol 
• 1261085-78-2 5-benzoyl-4,6-diphenyl-3,4-dihydro-2H-pyran-2-one 
• 1261085-79-3 5-benzoyl-6-methyl-4-phenyl-3,4-dihydro-2H-pyran-2-one 
• 94-41-7 benzalacetophenone 
• 98-86-2 acetophenone 
• 103-26-4 methyl cinnamate 
• 20577-73-5 methyl 4-phenyl-2,4-dioxobutanoate 
• 4475-13-2 (3-oxo-1,3-diphenyl-propyl)-malonic acid 
• 77670-30-5 diethyl 2-(3-oxo-1,3-diphenylpropyl)malonate 
• 103-26-4 Methyl cinnamate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 98-86-2 acetophenone 
• 103-26-4 methyl cinnamate 

Relevant academic research and scientific papers

DBU-Catalyzed Ring-Opening and Retro-Claisen Fragmentation of Dihydropyranones

We present a general protocol for the formal Michael addition of acetone to α,β-unsaturated esters and amides, a transformation difficult to perform using current methods. The protocol comprises of an amidine catalyzed relay ring-opening and fragmentation

Iodine(III)-Mediated Contraction of 3,4-Dihydropyranones: Access to Polysubstituted γ-Butyrolactones

Functionalized γ-butyrolactones are privileged structures in the field of medicinal chemistry; they are found in numerous natural products and synthetic compounds with diverse biological activities. The oxidative ring contraction of 3,4-dihydropyran-2-one derivatives represents a promising yet underappreciated strategy to access these compounds. To the best of our knowledge, very few examples of this strategy have been reported, with limited investigation of the influence of stereogenic centers on the starting dihydropyranones. We investigated the iodine(III)-mediated contraction of a representative set of dihydropyranone derivatives. The method gives rapid access to functionalized γ-butyrolactones in good yields. The reaction scope was investigated, and the method was found to support various levels of substituents, even enabling access to sterically congested quaternary centers. The stereoselectivity was investigated using chiral substrates and a chiral iodine(III) reagent.

PHOTOLABILE PRO-FRAGRANCES

Many fragrances that provide a scent of freshness tend to be highly volatile and are therefore not very economical when used in typical applications such as washing or cleaning processes, so they have to be used in relatively large quantities to be able to produce adequate effects. The disclosed photolabile pro-fragrances provide a much longer-lasting sense of fragrance, in particular with a scent of freshness, when used in typical applications, thus allowing said fragrances to be used efficiently.

The preparation of novel chiral auxiliaries SAMIQ/RAMIQ and their application in the asymmetric Michael addition

A pair of novel chiral auxiliaries SAMIQ/RAMIQ was synthesized from l- or d-phenylalanine methyl ester hydrochloride over six steps in 45.8% and 44.4% yield, respectively. The SAMIQ-/RAMIQ-hydrazone methodology was applied for the asymmetric Michael addit

Synthesis and reactivity of methyl 3-acyl-6-amino-4-aryl-5-cyano-4h-pyran- 2-carboxylates

By treating arylidenemalononitriles with methyl 2,4-dioxobutanoates, derivatives of 4H-pyrans - methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2- carboxylates - are obtained, which are novel, promising structural components for the synthesis of carbo- and

KF-alumina-mediated selective double Michael additions of aryl methyl ketones: A facile entry to the synthesis of functionalized pimelate esters and derivatives

Here we describe simple and efficient double Michael additions of aromatic and aliphatic methyl ketones to electron deficient alkenes promoted on a surface of KF-alumina. This one-pot procedure provides an easy access to a host of functionalized pimelate

Generation of organotantalum reagents and conjugate addition to enones

A superior method of conjugate allylation: The transmetalation of allyltin compounds with TaCl5 yielded active tantalum reagents for conjugate addition to enones. Even bulky allyl moieties could be introduced to enones in this manner (see scheme). Both cyclic and acyclic enones reacted facilely under extremely mild conditions.

Highly regioselective addition of an ester enolate equivalent to α,β-unsaturated ketones: Selective formation of both isomers derived from 1,2- and 1,4-additions using α-stannyl ester with additives

The reaction of α-stannyl ester with α,β-unsaturated ketones in the presence of stannous chloride (SnCl2) and chlorosilanes (Me3SiCl or Me2SiCl2) gave 1,2- and 1,4-addition products, respectively.

Synthesis and Stereochemistry of cis- and trans- 4,6-Diaryl-2-piperidones

Two-carbon 1,4-addition to variously substituted chalcones (3) and subsequent two-step reductive amination, and cyclisation via oxime intermediates resulsts in cis- (1) and trans- (2) 4,6-diarylpiperidones in high yields.The configuration and conformation