51547-88-7

Upstream product

• 52682-03-8 (S)(-)-N,O-bis(p-toluenesulphonyl)-2-hydroxymethyl pyrrolidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 81097-24-7 N-tosyl-(4-pentenyl)amine 
• 765-38-8 2-methyl-1-pyrrolidine 
• 108-27-0 5-methylpyrrolidin-2-one 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 144784-55-4 R-3-O-p-toluenesulfonyl-pentanenitrile 
• 144784-57-6 (S)-4-Phenylselanyl-pentanenitrile 
• 283610-03-7 (2R)-2-[(2'R)-2'-methyl-N-pyrrolidinyl]-2-phenyl-1-ethanol 
• 144784-59-8 4-Methyl-N-((S)-4-phenylselanyl-pentyl)-benzenesulfonamide 

Downstream Products

• 765-38-8 (R)-(-)-2-methylpyrrolidine 

Relevant academic research and scientific papers

Bis(trifluoromethanesulfonimide) (BSI): Acidity and application to hydrofunctionalization as a Br?nsted acid catalyst

A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Br?nsted acid. Computational prediction of the pKa value of BSI indicated its classification as a strong Br?nsted acid. BSI catalyzed the h

Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer

An enantioselective, radical-based method for the intramolecular hydroamination of alkenes with sulfonamides is reported. These reactions are proposed to proceed via N-centered radicals formed by proton-coupled electron transfer (PCET) activation of sulfonamide N-H bonds. Noncovalent interactions between the neutral sulfonamidyl radical and a chiral phosphoric acid generated in the PCET event are hypothesized to serve as the basis for asymmetric induction in a subsequent C-N bond forming step, achieving selectivities of up to 98:2 er. These results offer further support for the ability of noncovalent interactions to enforce stereoselectivity in reactions of transient and highly reactive open-shell intermediates.

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

Organocerium additions to proline-derived hydrazones: Synthesis of enantiomerically enriched amines

The addition of organocerium reagents (from both organolithium and organomagnesium precursors) to chiral aldehyde hydrazones prepared from 1-aminoproline derivatives has been studied. The additions proceed in good yield and high diastereoselectivity and with good nucleophile (Me, n-Bu, i-Pr, t-Bu, Ph, etc.) and substrate scope (alkyl, alkenyl and aryl). The resulting hydrazines can be converted to amines by N-N bond cleavage through hydrogenolysis (Raney nickel) or by acylation and cleavage with Li/NH 3. The influence of the side chain on the diastereoselectivity was investigated through variation of the substituents to include more coordinating atoms (oxygen and nitrogen) as well as the removal of coordinating atoms. The SAMEMP auxiliary bearing a 2-methoxyethoxymethyl group gave the highest diastereoselectivities. Remarkably, auxiliaries bearing simple methyl and isobutyl substituents gave high selectivities as well. Hypotheses for the origin of the selectivity are presented.

A simple stereoselective synthesis of enantiopure 2-substituted pyrrolidines and piperidines from chiral (R)-phenylglycinol-derived bicyclic 1,3-oxazolidines

Chiral, nonracemic 2-substituted pyrrolidines and piperidines were prepared in high ee and moderate to good chemical yields in three steps from (R)-phenylglycinol and γ- or δ-chloroketones. The key step of the synthesis was the stereo- selective reductive ring-opening of chiral bicyclic 1,3- oxazolidines prepared by condensation of (R)-phenylglycinol and the corresponding ketones.

Stereochemistry of the Intramolecular Substitution of Phenylselenonyl Group by Nitrogen Atom in Amide. Inversion of Configuration

The stereochemistry of the intramolecular substitution of phenylselenonyl group by a nitrogen atom in tosylamino group was proved to be inversion by the oxidative cyclization of (S)-1-alkyl-4-(tosylamino)butyl phenyl selenides to (R)-N-tosyl-2-alkylpyrrolidines.

Enantioselective Synthesis of Optically Pure Amino Alcohol Derivatives by Yeast Reduction

Baker's yeast reduction of nitro- and imide-containing ketones gives the corresponding secondary alcohols in good yields with excellent optical purity.Among the imide groups examined, the ketones with saccharin moiety give the products in the best chemical and optical yields.