1259319-79-3

Upstream product

• 1259319-70-4 cyanomethyl 4-bromobenzoate 
• 925-90-6 ethylmagnesium bromide 
• 586-76-5 4-Bromobenzoic acid 
• 1122-91-4 4-bromo-benzaldehyde 

Relevant academic research and scientific papers

Convenient and easy access to 2-hydroxycyclopent-2-enones from acylcyanohydrins

A convenient access to 2-hydroxycyclopentenones was designed from acylcyanohydrins, by using titanacyclopropane complexes as nucleophilic partners and an intramolecular aldol condensation in basic conditions. The development of a one-pot procedure allows a step- and atom-economic process, and the use of Grignard reagents other than ethylmagnesium bromide provided valuable 3,4-disubstituted 2-hydroxycyclopentenones. The utility of the hydroxy group was illustrated by further functionalization of the α-position using palladium-mediated cross-coupling reactions.

Titanium-mediated addition of grignard reagents to acyl cyanohydrins: Aminocyclopropane versus 1,4-diketone formation

The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition. The 1,2-dianion reactivity of the reagent generated from EtMgBr and Ti(OiPr)4 was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples). When the reaction was performed in diethyl ether, 1,4-diketones were mainly isolated. Under certain conditions, cyclopropane derivatives were also obtained in good yields. A mechanism rationalizing this dichotomy is presented. Copyright

TETRAHYDROPYRAN DGAT1 INHIBITORS

The invention relates to compounds of formula (I): useful for treating disorders mediated by acyl coA-diacylglycerol acyl transferase 1 (DGAT1), e.g. metabolic disorders. The invention also provides methods of treating such disorders, and compounds and compositions etc. for their treatment.

Titanium-mediated synthesis of 1,4-diketones from grignard reagents and acyl cyanohydrins

Double duty: In the presence of titanium isopropoxide, Grignard reagents were found to react with acyl cyanohydrins to give substituted 5-hydroxy-1,4-diketones (see scheme). This new reaction involves a formal addition of a 1,2-dianion equivalent to both the ester and nitrile moieties.