68487-09-2

Upstream product

• 4410-31-5 (RS)-mandelamide 
• 927-77-5 n-propylmagnesium bromide 
• 532-28-5 (RS)-mandelonitrile 
• 10557-57-0 propylmagnesium iodide 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 93-89-0 benzoic acid ethyl ester 
• 105-54-4 butanoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 50265-96-8 N-tert-butyl-N'-butylidenehydrazine 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 1569272-11-2 phenyl(2-propyl-1,3-dithian-2-yl)methanol 
• 123-72-8 butyraldehyde 
• 826-18-6 1-pentenylbenzene 
• 21663-35-4 1-phenyl-pent-3-ene-1,2-diol 

Relevant academic research and scientific papers

Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst

We found that chemoselectivity of the crossed acyloin product is controlled by the adjustment of the aromatic aldehyde/aliphatic aldehyde ratio. Moreover, we observed the persistent catalytic activity of the homogeneous NHC catalyst in a solution due to N

Synthesis of chiral α-diarylacetic esters by stereospecific 1,2-aryl migration promoted by in situ generated acetals from benzoins

A simple protocol for the synthesis of α-diarylacetic esters from benzoins is described. In situ generated acetal assists rapid 1,2-aryl migration in a stereospecific manner, paving the way to make enantioenriched α-diarylacetic esters from easily accessi

Polymer-supported synthesis of α- and β-hydroxyketones through the formation of 1,3-dithiane intermediates

The synthesis of polymer-supported 2-monosubstituted 1,3-dithianes from soluble copolymers bearing 1,3-propanedithiol groups, their lithiation, reactions with electrophiles such as aldehydes, ketones, α,β- unsaturated ketones and oxiranes, and cleavage of

Asymmetric reduction of α-keto esters and α-diketones with a bakers' yeast keto ester reductase

Optically pure α-hydroxy esters and α-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers' yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the stereochemical course depends on the chain length of the alkyl substituent on the carbonyl group. An α-keto short alkanoic ester affords the corresponding (S)-hydroxy ester, whereas a long alkanoate yields the corresponding (R)-hydroxy ester. The reduction of α-diketones affords the corresponding (S)-2-hydroxy ketones regio- and stereoselectively.

AZO ANIONS IN SYNTHESIS. PT 1. t-BUTYLHYDRAZONES AS ACYL-ANION EQUIVALENTS

The lithium salts of aldehyde t-butylhydrazones react with electrophiles (aldehydes, ketones, alkyl halides, crotonates) to form C-trapped t-butylazo-compounds; tautomerisation and hydrolysis gave α-hydroxy ketones, ketones, and γ-keto esters in good yield, thereby providing a convenient new acyl-anion equivalent.Reaction of these lithium salts with aldehydes and ketones, followed by elimination provided a new route to azo alkenes.

Azo Anions in Synthesis. t-Butylhydrazones as Acyl-anion Equivalents

The lithium salts of aldehyde t-butylhydrazones react with electrophiles (aldehydes, ketones, alkyl halides) to form C-trapped t-butylazo compounds; isomerisation and hydrolyse gave α-hydroxy ketones and ketones in good yields, thereby providing a convenient new acyl-anion equivalent.

A New Type of P-C and C-C Bond Cleavage Reactions in α-Trimethylsilyloxy-β-oxo Phosphonates and α-Ethoxy-β-oxo Phosphonates. The Synthesis of Unsymmetrical α-Hydroxy Ketones Utilizing 1:1 Carbonyl Adducts of Diethyl Trimethylsilyl Phosphite with Benzaldehyde

α-Lithiated diethyl α-(trimethylsilyloxy)benzylphosphonate underwent facile acylation with various acylating agents to afford the corresponding α-acylated products in good yields.On treatment with the α-acylated products with 1 M NaOH-EtOH (1:1, v/v) the P-C bond was cleaved with elimination of diethyl phosphate to give α-hydroxy ketones predominantly.On the other hand, when diethyl α-acyl-α-ethoxybenzylphosphonates were treated under the same conditions, they were rather stable and recovered.However, the prolonged alkaline treatment or the use of 4 M NaOH-EtOH (1:1 v/v) resulted in the C-C bond cleavage giving carboxylic acids and diethyl α-ethoxybenzylphosphonate in quantitative yields, respectively.The mechanisms of the above two reactions were proposed and discussed in connection with the Perkow reaction and related reactions.