109296-67-5

Upstream product

• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 300-57-2 allylbenzene 
• 100-34-5 benzene diazonium chloride 
• 107-18-6 allyl alcohol 
• 19261-37-1 2-chloro-3-phenyl-propionaldehyde 
• 2687-12-9 cinnamyl chloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 104-53-0 3-phenyl-propionaldehyde 
• 7474-06-8 2-chloro-3-phenylpropionic acid 
• 7497-19-0 (S)-2-chloro-3-phenyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

Novel ring-opening of epoxides and oxetanes with POCl3 or PCl3 in the presence of DMAP

Efficient synthesis of chlorohydrins by cleavage of oxiranes and oxetanes using POCl3 or PCl3 in the presence of DMAP (4-N,N-dimethylaminopyridine) has been studied.

A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1,1-dioxides

In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1,1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of

Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine

Herein we report a novel synthetic reaction to convert unactivated terminal aliphatic epoxide to alkyl vicinal dichloride based on triphosgene-pyridine activation. Our methodology is operationally simple and readily tolerated by a broad of scope of substrates as well as protecting groups. Furthermore, these mild conditions generally yield clean reaction mixtures that are free of byproducts upon aqueous workup.

Trichloromethanesulfonyl chloride: A chlorinating reagent for aldehydes

Trichloromethanesulfonyl chloride (CCl3SO2Cl), a commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.

Reaction of cinnamaldehyde and derivatives with Raney Ni-Al alloy and Al powder in water. Reduction or oxido-reduction?

A series of experiments dealing with the reduction of cinnamaldehyde and parent compounds was carried out in completely aqueous media in order to assess the character of this process. We wish to show that the treatment of these substrates in water with Raney catalysts is an oxido-reductive process.

Stereoselective synthesis of α,α-chlorofluoro carbonyl compounds leading to the construction of fluorinated chiral quaternary carbon centers

(Chemical Equation Presented) "F-antastic" chiral molecules: Asymmetric syntheses of α,α-chlorofluoro carbonyl compounds have been developed. Nucleophilic substitutions of an α,α- chlorofluoroketone thus obtained with azide or thiol nucleophiles provide v

Regioselective conversion of unsymmetrical terminal epoxides into vicinal chlorohydrins using dimethoxyboron chloride

A highly regioselective synthesis of chlorohydrins by chlorinative cleavage of unsymmetrical epoxides utilizing dimethoxyboron chloride is described. Except for styrene oxide, all the terminal epoxides were regioselectively cleaved following a predominantly SN2-type reaction pathway favouring the formation of primary chlorides. In the case of styrene oxide, a benzylic epoxide, (MeO)2BCl transfers the chlorine at the benzylic position, by following an apparent SN1-type mechanism. CSIRO 2006.

Direct Organocatalytic Asymmetric α-Chlorination of Aldehydes

The direct organocatalytic enantioselective α-chlorination of aldehydes has been developed. The reaction proceeds for a series of different aldehydes with NCS as the chlorine source using easily available catalysts such as L-proline amide and (2R,5R)-diphenylpyrrolidine. The α-chloro aldehydes are obtained in up to 99% yield and up to 95% ee. The synthetic utility of the enantioselective α-chlorination of aldehydes is demonstrated by transformation of the α-chloro aldehydes to the corresponding α-chloro alcohols (>90% yield) by standard reduction and further transformation to both a terminal epoxide and amino alcohol, both obtained without loss of optical purity. Oxidation of the α-chloro aldehydes followed by esterification gave optically active α-chloro esters without loss of optical purity. It is demonstrated that these optically active α-chloro esters can be converted into nonproteinogenic amino acids in overall high yields, maintaining the enantiomeric excess obtained in the catalytic enantioselective α-chlorination step. Copyright

1,2-Ferrocenediylazaphosphinines 2: A new class of nucleophilic catalysts for ring-opening of epoxides

1,2-Ferrocenediylazaphosphinines (1a-c) have been successfully employed as a new class of nucleophilic catalysts for ring-opening of a range of epoxides, their catalytic efficiency in terms of regioselectivity as well as chemical yield comparing well with the existing catalysts in the literature. In contrast, low enantiomeric excesses have been obtained from the reactions of meso-epoxides catalyzed by (R)-1.

Demonstration of a phosphazirconocene as a catalyst for the ring opening of epoxides with TMSCI

(Matrix presented) In this study, it was demonstrated for the first time that a phosphazirconocene catalyzes the ring opening of epoxides with TMSCI. This reactivity leads to a facile preparation of chlorohydrins. The late transition metal Fe analogue was found to catalyze the reaction at rates and stereoselectivity comparable to those of the Zr complex.