718633-51-3

Upstream product

• 13379-98-1 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol 
• 59724-53-7 (±)-N-(2-hydroxypropyl)-4-methylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 107-02-8 acrolein 
• 164532-58-5 N-(p-tosyl)-3-aminopropionaldehyde diethyl acetal 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 41365-75-7 aminopropane diethyl acetal 

Downstream Products

• 405932-40-3 (E)-2-bromo-5-[N-(4-methylphenylsulfonyl)amino]pent-2-enoate 
• 405932-38-9 (Z)-2-bromo-5-[N-(4-methylphenylsulfonyl)amino]pent-2-enoate 
• 161040-05-7 N-(but-3-yn-1-yl)-4-methylbenzenesulfonamide 
• 910050-88-3 6-(10-bromodecyl)-4-chloro-1-tosyl-1,2,3,6-tetrahydropyridine 

Relevant academic research and scientific papers

Phosphine-Catalyzed Synthesis of Chiral N-Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling

Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.

Phosphine-Catalyzed (4 + 2) Annulation of δ-Sulfonamido-Substituted Enones with 1,1-Dicyanoalkenes: Synthesis of Piperidine Derivatives

The δ-sulfonamido-substituted enones were employed as phosphine acceptor in phosphine-catalyzed (4 + 2) annulation of 1,1-dicyanoalkenes. They served as a four-membered synthon to react with 1,1-dicyanoalkenes under mild reaction conditions, producing pip

Chemo- And diastereoselective synthesis of pyrrolidines from aroylformates and δ-tosylamino enones via P(NMe2)3-mediated reductive amination/base-catalyzed michael addition cascade

A novel P(NMe2)3-mediated tandem (1 + 4) annulation between aroylformates and δ-tosylamino enones has been developed that affords a facile synthesis of functionalized pyrrolidines in moderate to excellent yields with exclusive chemoselectivity and high diastereoselectivity. Mechanistic investigation reveals that the reaction proceeds through an unprecedented P(NMe2)3-mediated reductive amination/base-catalyzed Michael addition cascade. The reaction herein also represents the first study of the reactivity patterns of the Kukhtin-Ramirez adducts toward ambiphilic nucleophile-electrophiles.

Organocatalyzed Aerobic Oxidation of Aldehydes to Acids

The first example organocatalyzed aerobic oxidation of aldehydes to carboxylic acids in both organic solvent and water under mild conditions is developed. As low as 5 mol % N-hydroxyphthalimide was used as the organocatalyst, and molecular O2 was used as the sole oxidant. No transition metals or hazardous oxidants or cocatalysts were involved. A wide range of carboxylic acids bearing diverse functional groups were obtained from aldehydes, even from alcohols, in high yields.

Allylation of aldehydes by dual photoredox and nickel catalysis

Here we report the application of dual nickel/photoredox catalysis to the allylation of aliphatic, aromatic and heteroaromatic aldehydes by using commercially available reagents. The process utilizes the combination of a Ni(ii) complex, [Ru(bpy)3]2+ as a photoredox catalyst, and allylacetate under blue LED irradiation, and allows the synthesis of a large variety of homoallylic alcohols.

One-Pot Synthesis of Cyclopropanes from Methylene Azabicyclo[3.1.0]hexanes Obtained by Formal Sequential [1+2]- and [2+3]-Cycloaddition Reaction of Prop-2-ynylsulfonium Salts and Tosylaminomethyl Enones

A formal sequential [1+2]- and [2+3]-annulation of prop-2-ynylsulfonium salts and tosylaminomethyl enones was developed, constructing a series of methylene azabicyclo[3.1.0]hexane derivatives. A one-pot procedure was established via hydration of an enamine intermediate to afford substituted cyclopropanes. Prop-2-ynylsulfonium salts acted as both C2 and C1 synthons in these two processes. (Figure presented.).

ENANTIOSELECTIVE SYNTHESES OF HETEROYOHIMBINE NATURAL PRODUCT INTERMEDIATES

Enantioselective syntheses of cis- and trans-bicyclic dihydropyran compounds, and other intermediates, en route to heteroyohimbine alkaloids.

Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis

Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as "anhydronium bases") containing three contiguous stereocenters. Each possesses interesting biological activity, with alstonine being the major component of a plant-based remedy to treat psychosis and other nervous system disorders. This work describes the enantioselective total syntheses of these natural products with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step. The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.

Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines

A bifunctional squaramide catalysed aza-Michael/Michael cascade reaction between nitroalkenes and tosylaminomethyl enones or enoates has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chiral pyrrolidines with a broad substrate scope, giving the desired products in good yields (up to 99%) with good diastereoselectivities (up to 91 : 9 dr) and excellent enantioselectivities (up to >99% ee) under mild conditions. This protocol provides a straightforward entry to highly functionalized chiral trisubstituted pyrrolidine derivatives from simple starting materials.

Chiral pyrrolidines and piperidines from enantioselective rhodium-catalyzed cascade arylative cyclization

A new rhodium-catalyzed asymmetric arylative cyclization of nitrogen-tethered alkyne-enoate with arylboronic acids is described. In this process two new carbon-carbon bonds and one stereocenter are formed, providing access to pyrrolidines and piperidines