141248-89-7

Upstream product

• 151-50-8 potassium cyanide 
• 136132-07-5 3-(bromomethyl)-3-phenyl-1,2-dioxetane 
• 591-51-5 phenyllithium 
• 87234-28-4 1,3-dichloro-2-hydroxy-2-phenylpropane 
• 191479-39-7 3-chloro-2-phenyl-1,2-propanediol 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 1005-91-0 2-phenyl-2-(chloromethyl)oxirane 
• 139-66-2 diphenyl sulfide 

Downstream Products

• 152774-05-5 (S)-(2-phenyloxiran-2-yl)methanol 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 1609086-34-1 3-morpholino-2-phenylpropane-1,2-diol 
• 191479-39-7 3-chloro-2-phenyl-1,2-propanediol 
• 1609085-78-0 2-phenyl-3-(phenylamino)propane-1,2-diol 
• 191479-65-9 (R)-2-Methoxymethyl-2-phenyl-oxirane 

Relevant academic research and scientific papers

Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides

We report the direct preparation of 1,3-amino alcohols that contain up to three contiguous stereogenic centers by the umpolung coupling of imines and epoxides. Nucleophilic 2-azaallyl anions, generated from imines, are stereoselectively added to epoxides to furnish 1,3-amino alcohols after hydrolysis of the product imine. Transformations afford amino alcohols with >98% site selectivity with respect to both reaction partners and in up to >98% yield and >20:1 dr.

Regioselective bromocyclization of unsaturated N-tosylcarbamates promoted by N, N-dibromosulfonamides

Simple and highly regioselective bromo-N-cyclization and bromo-O-cyclization reactions of unsaturated N-tosylcarbamates have been developed. The use of N,N-dibromosulfonamides as brominating reagents plays an important role in these electrophilic cyclizat

Asymmetric autocatalysis triggered by carbon isotope (13 C/12C) chirality

Many apparently achiral organic molecules on Earth may be chiral because of random substitution of the 1.11% naturally abundant 13C for 12C in an enantiotopic moiety within the structure. However, chirality from this source is experimentally difficult to discern because of the very small difference between 13C and 12C. We have demonstrated that this small difference can be amplified to an easily seen experimental outcome using asymmetric autocatalysis. In the reaction between pyrimidine-5-carbaldehyde and diisopropylzinc, addition of chiral molecules in large enantiomeric excess that are, however, chiral only by virtue of isotope substitution causes a slight enantiomeric excess in the zinc alkoxide of the produced pyrimidyl alkanol. Asymmetric autocatalysis then leads to pyrimidyl alcohol with a large enantiomeric excess. The sense of enantiomeric excess of the product alcohol varies consistently with the sense of the excess enantiomer of the carbon isotopically chiral compound.

An improved method for the addition reactions of 1,3-dichloroacetone with combined organolithium-cerium trichloride reagents

Alkyl-, phenyl- and alkynyllithium reagents in combination with anhydrous cerium(III) chloride underwent addition reactions with 1,3-dichloroacetone in a very efficient manner. The addition products are versatile precursors for 2-substituted epichlorohydrins and glycidols. Fluconazole, a potent antifungal agent, was thus synthesized in 67% yield by addition of 1,3-dichloroacetone to 2,4-difluorophenyllithium in the presence of cerium(III) chloride, followed by substitution of the chlorine atoms with 1,2,4-triazole.

Reaction of 1,2-dioxetanes with heteroatom nucleophiles: Adduct formation by nucleophilic attack at the peroxide bond

The reactions of 3,3-disubstituted 1,2-dioxetanes 1 with numerous heteroatom nucleophiles, e.g., R2NH, R3N, RSH, R2S, CN-, SCN-, Br-, Cl-, OH-, and O2*-, were investigated. Initial nucleophilic substitution at the sterically less hindered site of the dioxetane peroxide bond leads to addition, deoxygenation, and fragmentation products. The observed SN2 chemistry was substantiated with the dioxetane le because bromide ion displacement by the proximate alkoxide ion site afforded epoxide products. Thus, with anionic nucleophiles the epoxy alcohol 8c was obtained in appreciable amounts, and triethylamine and DABCO gave with 1c exclusively the alkoxyammonium epoxides 4c and 5c. Moreover, the labile alkoxysulfonium epoxide 6c was detected as an intermediate in the deoxygenation of 1c by diphenyl sulfide. From the reaction of 1b-d with secondary amines were isolated the hydroxylamine derivatives 2 and 3, and the cyanide and thiocyanate ions gave with 1c,d five-membered-ring insertion products, namely, the carbonates 9c,d and the cyclic sulfite 10c.