14252-67-6

Upstream product

• 104897-97-4 (S)-Chloro-phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 134933-56-5 (S)-Chloro(phenyl)acetaldehyde 
• 10606-73-2 (S)-2-chloro-2-phenylacetic acid ethyl ester 
• 20780-53-4 (R)-Styrene oxide 
• 110743-96-9 (R)-2-(tert-butyldimethylsilyloxy)-1-phenylethan-1-ol 
• 331991-04-9 (S)-2-chloro-2-phenyl-acetic acid pentachlorophenyl ester 
• 21306-21-8 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one 
• 103-80-0 phenylacetyl chloride 
• 104897-86-1 Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104897-90-7 N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((Z)-2-phenyl-1-trimethylsilanyloxy-vinyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide 
• 611-71-2 (R)-Mandelic Acid 
• 10606-72-1 (R)-mandelic acid ethyl ester 
• 4638-79-3 2-chloro-2-phenylacetaldehyde 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 

Downstream Products

• 20780-53-4 (R)-Styrene oxide 
• 20780-54-5 (S)-styrene oxide 

Relevant academic research and scientific papers

Selective monochlorination of unsymmetrical vicinal diols with chlorinated iminium chlorides

Chlorinated iminium chlorides have been identified to promote the highly efficient and selective mono-chlorination of unsymmetrical vicinal diols. Vilsmeier reagent, namely, (chloromethylene)dimethyliminium chloride, enables highly reactive and regioselective chlorination of 1,2- and 1,3-diols featured one secondary benzylic hydroxy group and one primary aliphatic hydroxy group to give the corresponding 1,2- and 1,3-chlorohydrins. Viehe's salts (α,α-dichloro iminium salts) exhibit excellent reactivity and good selectivity for vicinal diols to give the corresponding chlorohydrin carbamates via a cyclic intermediate in situ. The chlorination protocols tolerate diverse functional groups, including halogens, naphthalene rings, nitro, and cyano. Moreover, the optical purity of chiral diols could be retained during this chlorination reaction.

Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution

In a previous study it was shown that the enantioselective α-fluorination of racemic α-chloroaldehydes with a chiral organocatalyst yielded the corresponding α-chloro-α-fluoroaldehydes with high enantioselectivity. It was also revealed that kinetic resolu

Catalytic, Asymmetric α-Chlorination of Acid Halides

We present a full account of a tandem catalytic, asymmetric chlorination/esterification process that produces highly optically enriched α-chloroesters from inexpensive, commercially available acid halides using cinchona alkaloid derivatives as catalysts and polychlorinated quinones as halogenating agents. We have performed kinetics and control experiments to investigate the reaction mechanism and establish conditions under which the reactions can be best performed. We have developed NaH and NaHCO3 shuttle base systems as the easiest and most cost-effective ways of conducting the reactions, rendering the methodology economically competitive with known chiral halogenation procedures. We have also demonstrated the utility of our reactions by converting the products to synthetically useful derivatives.

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.

Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to β-halohydrins with lithium halides

The reaction of epoxides with lithium halides was efficiently promoted on the surface of silica gel in the absence of any solvent to give the corresponding β-halohydrins. The reactivity of lithium halides was shown to follow the order LiI > LiBr >> LiCl, and the reactivity of LiCl was dramatically increased by adding an equivalent amount of water to this system. On the other hand a similar reaction with α,β-epoxyketones produces the α-haloenone derivatives, presumably via halohydrin intermediates. The epoxide-opening reaction of (R)-(+)-styrene oxide was also investigated to clarify the stereochemical features of this reaction.

Kinetic Resolution of Racemic Aldehydes by Enantioselective Alkylation

Various types of racemic aldehydes were kinetically resolved with diethylzinc in the presence of a catalytic amount of a chiral β-amino alcohol.Kinetic resolution of racemic chloro(phenyl)acetaldehyde gave an optically active form as an unchanged substrate, which could be converted into styrene oxide in high optical purity (97.5percent ee).

ASYMMETRIC HALOGENATION OF CAMPHOR-10-SULFONIC ACID DERIVED ESTERS: AN EFFICIENT NEW ROUTE TO ENANTIOMERICALLY PURE HALOHYDRINS AND EPOXIDES.

Successive treatment of chiral esters 1 with LDA/Me3SiCl and NBS or NCS gave crystalline α-haloesters 3 which furnished halohydrins 4 and terminal epoxides 5 in high e.e..