257952-52-6

Upstream product

• 79-24-3 Nitroethane 
• 100-52-7 benzaldehyde 
• 1663-61-2 triethoxymethylbenzene 
• 98-88-4 benzoyl chloride 
• 492-41-1 (1R,2S)-norephedrine 
• 873-66-5 1-propenylbenzene 
• 5267-71-0 (1R,2S)-N-(2-hydroxy-1-methyl-2-phenylethyl)benzamide 

Downstream Products

• 2153-98-2 (-)-Norpseudoephedrine hydrochloride 

Relevant academic research and scientific papers

A biocatalytic Henry reaction - The hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions

(Figure Presented) Novel enzyme activity: Biocatalytic Henry reactions with nitromethane and nitroethane yielded the corresponding nitroalcohols with good enantio- and diastereo-control in the presence of the hydroxynitrile lyase from the tropical rubber tree Hevea brasiliensis. Molecular modeling and deuterated starting materials were used in mechanistic investigations.

Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide

Heating N-(β-hydroxyethyl)amides with DIC and Cu(OTf)2 (5 mol %) leads to the formation of 2-oxazolines in good to excellent yields. N-(β-Hydroxy)amides can be cyclised by reaction with diisopropylcarbodiimide (DIC) to give the corresponding 2-

Asymmetric N1 unit transfer to olefins with a chiral nitridomanganese complex: Novel stereoselective pathways to aziridines or oxazolines

Chiral nitridomanganese complex 1 was found to be a highly potential N1 unit source for the asymmetric synthesis of aziridines and 2-oxazolines from olefins such as styrene and its derivatives. When sulfonyl chlorides were employed as activators of the complex in the presence of pyridine, pyridine N-oxide, and a silver salt, the reaction of olefins with complex 1 proceeded smoothly to afford the N-sulfonylated aziridines. The aziridination of styrene derivatives with complex 1 using 2-trimethylsilylethanesulfonyl chloride (SESC1) gave the N-SES-aziridines, which were easily converted into chiral N-unsubstituted aziridines. It was found that the reaction was applicable to the asymmetric synthesis of 2-oxazolines from olefins when acyl chlorides were employed as activators. Complex I provided an effective asymmetric environment for trans-disubstituted styrenes in the reaction (up to 92% ee). This is the first example of a direct asymmetric synthesis of 2-oxazolines from olefins. Additional experiments, conducted during the course of this investigation, suggest that the isomerization of the N-acylaziridine intermediate is involved in this reaction.

Direct asymmetric synthesis of oxazolines from olefins using a chiral nitridomanganese complex: A novel three-component coupling leading to chiral oxazolines

A new synthetic method for chiral oxazolines has been developed by N1 unit transfer to olefins using a chiral nitridomanganese complex. When trans-disubstituted styrenes were treated with chiral complex 1 in the presence of an acid chloride, oxazolines we

Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a meso-cyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudoephedrine was developed.