221196-89-0

Upstream product

• 51076-95-0 2-chloro-1,1,1-triethoxyethane 
• 56613-80-0 D-2-phenylglycinol 
• 116173-81-0 (R)-2-methyl-4-phenyl-Δ²-oxazoline 
• 107-14-2 chloroacetonitrile 
• 36743-66-5 ethyl chloroacetimidate hydrochloride 
• 70737-12-1 methyl 2-chloroacetimidate hydrochloride 

Downstream Products

• 1259027-36-5 1-{[(4R)-phenyl-4,5-dihydro-1,3-oxazol-2-yl]methyl}-3-mesityl-1H-imidazol-3-ium chloride 
• 832117-31-4 2-methyl-2-(1-methyl-1H-indol-3-yl)-1((R)-4-phenyl-4,5-dihydrooxazol-2-yl)propan-1-ol 
• 832117-32-5 (R)-(+)-3-[1-methyl-1-(1-methyl-1H-indol-3-yl)ethyl]-5-phenyl-5,6-dihydro[1,4]oxazin-2-one 
• 832117-30-3 (R)-2-(1,2-epoxy-2-methyl)propyl-4-phenyloxazoline 

Relevant academic research and scientific papers

Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate

A simple approach to a diverse set of chiral trisoxazolines is described. Deprotonation of bisoxazolines 2, followed by treatment of 2- chloromethyloxazolines 3, affords chiral trisoxazolines, including chiral homo- and hetero-trisoxazolines in good to hi

A Novel Bisoxazoline-Imidazolium Salt in Ytterbium-Catalyzed Asymmetric Reduction of Ketone

Chiral N-heterocyclic carbene (NHC), a privileged ligand for transition metals, has had a profound impact on organometallic chemistry. The monodentate and bidentate chiral carbenes have been developed significantly, while the tridentate ones have been less exploited. Herein, we designed and synthesized a new bisoxazoline-imidazolium salt as a carbene precursor, which owns three chelating sites and two kinds of chiral information centers. A preliminary investigation on the asymmetric ketone reduction was also studied.

Imidazolium-oxazoline salts in ruthenium-catalyzed allylic substitution and cross metathesis of formed branched isomers

Imidazolium-oxazoline chlorides have been prepared from chloroacetonitrile and used to generate bidentate mixed NHC-oxazoline ligands for ruthenium-catalyzed substitution of cinnamyl chloride by phenols. These ligands associated to [RuCp*(MeCN)3][PF6] promote allylic substitution reactions at room temperature with high regioselectivity in favour of the branched isomers giving terminal alkenes. These allylic ethers have been involved in further ruthenium-catalyzed cross metathesis reactions with electron-deficient olefins to give unsaturated esters and aldehydes. NHC-oxazoline ligands associated to the Cp*RuII moiety generate catalysts that orientate the nucleophilic allylic substitution of cinnamyl chloride by phenols towards the regioselective formation of branched products, which, on reaction with Hoveyda(II) catalyst, lead to cross metathesis, and unsaturated functional compounds.

Synthesis of optically active 2-chloromethyl-2-oxazolines by the ortho- ester condensation method using triethyl orthochloroacetate

A set of optically active 2-chloromethyl-2-oxazolines was synthesized by condensation of optically active 2-amino alcohols with triethyl orthochloroacetate which was prepared conveniently from triethyl orthoacetate by chlorination using tert-butyl hypochlorite.