87769-52-6

Upstream product

• 1694-31-1 tert-butyl acetoacetate 
• 100-39-0 benzyl bromide 
• 59832-42-7 2-Benzyliden-acetessigsaeure-tert-butylester 

Downstream Products

• 91956-52-4 4-benzyl-5-oxo-hexanenitrile 
• 1158184-30-5 (S,E)-2-acetyl-2-benzyl-5-oxo-hex-3-enoic acid tert-butyl ester 
• 850147-87-4 tert-butyl α-benzyl-α-diazoacetate 
• 1191108-89-0 (S)-tert-butyl 2-benzyl-2-(hydroxymethyl)-3-oxobutanoate 
• 1262669-63-5 (S)-tert-butyl 2-acetyl-2-benzyl-4-nitrobutanoate 
• 1432601-97-2 (R)-tert-butyl 2-((R)-4-methyl-3-oxocyclohex-1-enyl)-3-phenylpropanoate 
• 1432602-01-1 (R)-tert-butyl 2-(3-oxocyclohept-1-enyl)-3-phenylpropanoate 
• 1432602-09-9 (R)-tert-butyl 2-(3-oxocyclopent-1-enyl)-3-phenylpropanoate 
• 1432601-65-4 (R)-tert-butyl 2-(3-oxocyclohex-1-enyl)-3-phenylpropanoate 
• 1432601-89-2 (R)-tert-butyl 2-(5,5-dimethyl-3-oxocyclohex-1-enyl)-3-phenylpropanoate 

Relevant academic research and scientific papers

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.

Catalytic Enantioselective Protonation/Nucleophilic Addition of Diazoesters with Chiral Oxazaborolidinium Ion Activated Carboxylic Acids

A new chiral Br?nsted acid derived from carboxylic acid and a chiral oxazaborolidinium ion (COBI), as an activator, is introduced. This acid was successfully applied as a catalyst for the highly enantioselective protonation/nucleophilic addition of diazoesters with carboxylic acids.

Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: Efficient synthesis of functionalized 2-pyrazolines

Highly enantioselective 1,3-dipolar cycloaddition reactions of α-substituted diazoacetates are accomplished by catalysis of the chiral oxazaborolidinium ion. Functionalized 2-pyrazolines are synthesized in high to excellent enantiomeric ratios (up to >99:

Iron(iii)-salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles

Chiral iron(iii)-salan complexes catalysed highly enantioselective α-fluorination and α-hydroxylation of β-keto esters and N-Boc oxindoles to give the corresponding products in high yields and good-to-excellent ee values under mild reaction conditions. This journal is the Partner Organisations 2014.

Catalytic carbon insertion into the β-vinyl C-H bond of cyclic enones with alkyl diazoacetates

The first example of the boron Lewis acid catalyzed Csp2-H functionalization of cyclic enones was achieved using diazoacetates. The insertion of the carbon atom of diazoacetates utilizes BF3? Et2O or a newly designed oxaza

Catalytic enantioselective carbon insertion into the β-vinyl C-H bond of cyclic enones

Chiral oxazaborolidinium ion-catalyzed Csp2-H functionalization of enones using diazoacetate has been developed. Various β-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99%

Enantioselective synthesis of α-alkyl-β-ketoesters: Asymmetric Roskamp reaction catalyzed by an oxazaborolidinium ion

Breaking kamp: A catalytic route toward chiral α-alkyl-β- ketoesters using the title reaction of α-alkyl diazoester with aldehydes has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities and this methodology was applied to a concise two-step synthesis of the natural pheromone sitophilate. Copyright

Highly enantioselective chlorination of β-keto esters and subsequent SN2 displacement of tertiary chlorides: A flexible method for the construction of quaternary stereogenic centers

Highly enantioselective chlorination of β-oxo esters and subsequent stereospecific substitution of tertiary chlorides are described. Enantioselective chlorination of β-keto esters and malonates was performed using a chiral Lewis acid catalyst prepared from Cu(OTf)2 and the newly developed spirooxazoline ligand 2 to yield the desired α-chlorinated products with high enantioselectivity (up to 98% ee). Nucleophilic substitution of the resulting chlorides proceeded smoothly to afford a variety of chiral molecules such as α-amino, α-alkylthio, and α-fluoro esters, without loss of enantiopurity. The results of X-ray crystallographic analysis proved that Walden inversion occurs at the chlorinated tertiary carbon center. These results supported the fact that the substitution proceeds via an S N2 mechanism.

Desymmetrizing asymmetric ring expansion of cyclohexanones with α-diazoacetates catalyzed by chiral aluminum Lewis acid

Chiral aluminum Lewis acid catalyst composed of Me3Al and 3,3′-bis(trimethylsilyl)-BINOL in a 2:1 ratio was found to promote novel catalytic asymmetric ring expansion of cyclohexanone with α-substituted α-diazoacetates to give seven-membered rings with an all-carbon quaternary center. Application of this strategy to 4-substituted cyclohexanones opened up a novel way for the catalytic desymmetrizing asymmetric construction of cycloheptanones bearing remote α,δ-chiral centers.

Catalytic asymmetric roskamp reaction of α-Alkyl-α-diazoesters with aromatic aldehydes: Highly enantioselective synthesis of α-Alkyl-β-keto esters

The first catalytic enantioselective Roskamp reaction of α-alkyl-α-diazoesters with aromatic aldehydes was realized using a simple chiral N, N′-dioxide-scandium(III) complex. Remarkably, with 0.05 mol % catalyst, the reaction was performed well over a series of substrates, giving the desired products chemoselectively in excellent yields (up to 99%) and enantioselectivities (up to 98% ee) under mild conditions. This protocol provides a promising method for the synthesis of chiral α-alkyl-β- keto esters and 1,3-diols.