160224-49-7

Upstream product

• 930-68-7 cyclohexenone 
• 75-52-5 nitromethane 
• 1226508-79-7 ethyl 2-nitro-2-((R)-3-oxocyclohexyl)acetate 
• 1353763-37-7 ethyl 2-nitro-2-(3-oxocyclohexyl)acetate 

Downstream Products

• 196790-44-0 (1S,3R)-3-nitromethylcyclohexanol 

Relevant academic research and scientific papers

Chiral Vicinal Diamines Derived from Mefloquine

Novel 1,2-diamines based on the mefloquine scaffold prepared in enantiomerically pure forms resemble 9-amino-Cinchona alkaloids. Most effectively, 11-aminomefloquine with an erythro configuration was obtained by conversion of 11-alcohol into azide and hydrogenation. Alkylation of a secondary amine unit was needed to arrive at diastereomeric threo-11-aminomefloquine and to introduce diversity. Most of the substitution reactions of the hydroxyl group to azido group proceeded with net retention of the configuration and involved actual aziridine or plausible aziridinium ion intermediates. Enantiomerically pure products were obtained by the resolution of either the initial mefloquine or one of the final products. The evaluation of the efficacy of the obtained vicinal diamines in enantioselective transformations proved that erythro-11-aminomefloquine is an effective catalyst in the asymmetric Michael addition of nitromethane to cyclohexanone (up to 96.5:3.5 er) surpassing epi-aminoquinine in terms of selectivity.

A versatile approach to functionalized cyclic ketones bearing quaternary carbon stereocenters via organocatalytic asymmetric conjugate addition of nitroalkanes to cyclic β-substituted α,β-Enones

A versatile organocatalytic asymmetric conjugate addition of nitroalkanes to β-substituted cyclic α,β-enones to yield cyclic ketones bearing all-carbon quaternary stereogenic centers at β-C has been developed. This is an extension of the method that we de

Asymmetric Conjugate Addition of Nitroalkanes to Enones Using a Sulfonamide-Thiourea Organocatalyst

The asymmetric conjugate addition of nitroalkanes to α,β-unsaturated ketones in the presence of a catalytic amount of a novel sulfonamide-thiourea organocatalyst resulted in the corresponding γ-nitro carbonyl products in high yields with excellent enantio

Organocatalytic enantioselective Michael addition of α-nitroacetate to α,β-unsaturated enones: A route to chiral γ-nitro ketones and δ-keto esters

The catalytic enantioselective conjugate addition reaction of α-nitroacetate to α,β-unsaturated enones promoted by chiral bifunctional organocatalysts is described. The treatment of α-nitroacetate to α,β-unsaturated enones afforded the corresponding Micha

Enantioselective conjugate addition of nitro compounds to α,β-unsaturated ketones: An experimental and computational study

A series of chiral thioureas derived from easily available diamines, prepared from α-amino acids, have been tested as catalysts in the enantioselective Michael additions of nitroalkanes to α,β-unsaturated ketones. The best results are obtained with the bi

Primary amine/(+)-CSA salt-promoted organocatalytic conjugate addition of nitro esters to enones

The combination of 9-amino-9-deoxy-epi-cinchonine and (+)-CSA resulted in a novel primary amine-based organocatalyst for effective iminium activation of α,β-unsaturated ketones. Such a catalytic system could catalyze the conjugate addition of nitroacetate

Enantioselective organocatalytic conjugate addition of α-nitroacetate to α,β-unsaturated ketones in water

The catalytic enantioselective conjugate addition reaction of α-nitroacetate to α,β-unsaturated ketones promoted by chiral bifunctional organocatalysts is described. The treatment of α-nitroacetate to α,β-unsaturated ketones under aqueous-phase reaction c

Highly enantioselective michael addition of nitroalkanes to chalcones using chiral squaramides as hydrogen bonding organocatalysts

A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low cata

Synthesis and evaluation of guanidinyl pyrrolidines as bifunctional catalysts for enantioselective conjugate additions to cyclic enones

Guanidinyl pyrrolidines derived from 'S'-proline are effective catalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cyclohexenone and cyclopentenone in the absence of basic additive

Asymmetric conjugate addition of nitroalkanes to enones with a chiral α-aminophosphonate catalyst

Chiral diethyl (2R)-tetrahydropyrro-2-ylphosphonate is an effective catalyst for the Michael addition of nitroalkanes to α,β-unsaturated ketones. This study revealed that the hydrate salt of this α-aminophosphonate was found to be a better catalytic speci