16780-44-2

Upstream product

• 10552-65-5 4-methyl-N-(tetrahydro-2H-pyran-2-yl)benzenesulfonamide 
• 68820-06-4 5-(p-Tolylsulfonylamino)-4-phenylthiopentan-1-ol 
• 23438-61-1 1-(toluene-4-sulfonyl)piperidin-2-one 
• 95769-37-2 5-hydroxypentyl p-toluenesulfonate 
• 70-55-3 toluene-4-sulfonamide 
• 142-68-7 TETRAHYDROPYRANE 
• 2508-29-4 5-hydroxypentylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1402581-07-0 N-(4-methoxybenzyl)-N-(5-(4-methoxybenzyloxy)pentyl)-4-methylbenzenesulfonamide 
• 1402581-09-2 N-(5-hydroxypentyl)-N-(4-methoxybenzyl)-4-methylbenzenesulfonamide 
• 675-20-7 piperidin-2-one 
• 28833-59-2 C₂₆H₂₄N₂O₄S₄ 

Downstream Products

• 68820-08-6 N,O-Di-p-toluolsulfonyl-5-amino-pentanol-⁽¹⁾ 
• 4703-22-4 N-tosylpiperidine 
• 898827-97-9 hex-5-ynoic acid 5-(toluene-4-sulfonylamino)-pentyl ester 
• 145472-40-8 1-(toluene-4-sulfonyl)-piperidin-2-ol 
• 898827-99-1 7-(toluene-4-sulfonyl)-1-oxa-7-aza-cyclotridec-8-yn-13-one 
• 898827-98-0 6-bromo-hex-5-ynoic acid 5-(toluene-4-sulfonylamino)-pentyl ester 
• 1239988-05-6 N-[5-(tert-butyldimethylsilyloxy)pentyl]-tosylamide 
• 1376282-61-9 C₁₈H₃₃NO₃SSi 
• 1376282-62-0 C₂₃H₄₁NO₅SSi 
• 1376282-63-1 tert-butyl (5-oxopentyl)(tosyl)carbamate 
• 1376282-64-2 C₂₀H₂₉NO₅S 
• 1376282-37-9 C₂₀H₃₁NO₅S 
• 23438-61-1 1-(toluene-4-sulfonyl)piperidin-2-one 
• 81097-36-1 1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine 

Relevant academic research and scientific papers

Synthesis and Structural Elucidation of 1,2-Disubstituted 3-Fluoropiperidines

The work described details the reaction between Selectfluor and a series of 1-carbonyloxy and 1-sulfonyl 2-piperidines in order to generate 3-fluoro-2-methoxypiperidines 3a–f. Their subsequent reaction with allyltrimethylsilane, in the presence of BF3 and TiCl4, is then reported. Studies involving a combination of single-crystal X-ray crystallography and NMR spectroscopy indicate that the allylation process is cis-selective for both carbamate and sulfonamide variants and that optimal levels of diastereoselectivity are obtained using the N-2-nitrobenzene sulfonyl (2-Ns) group. In this manner, the synthesis of a series of 2-allyl 3-fluoro-substituted piperidines (5a, c–f) was achieved. The conversion of both the cis and trans-N-tosyl adducts (5d) into 3-fluorinated analogues of the natural products pelletierine (10) and coniine (11) is subsequently detailed.

Lewis Acid Catalyzed Electrophilic Aminomethyloxygenative Cyclization of Alkynols with N, O-Aminals

Lewis acid enables the electrophilic carbooxygenative cyclization of alkynols with N,O-aminals. The new process proceeds efficiently under very mild conditions via a pathway that is opposite to classical carbo-metalation. These reactions exhibit broad substrate generality and functional group compatibility, leading to a wide variety of 5-8-membered oxacycles bearing diverse functional groups. The cyclization products can be elaborated via simple functional group transformations to generate synthetically useful oxacycles.

Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols

By using the commercially available ruthenium pincer complex (Ru-MACHO-BH) as a catalyst, the challenging direct hydrogenation of lactams and analogues has been successfully accomplished to deliver corresponding value-added amino alcohols in good-to-excellent yields under mild reaction conditions. Remarkably, in addition to N-protected lactams, unprotected ones could also be readily reduced in the presence of a catalytic amount of weak base or even under neutral reaction conditions, which further highlights the broad substrate scope and the protocol efficiency.

Laccase/2,2,6,6-tetramethylpiperidinoxyl radical (TEMPO): An efficient catalytic system for selective oxidations of primary hydroxy and amino groups in aqueous and biphasic media

Copper salts/2,2,6,6-tetramethylpiperidinoxyl radical (TEMPO) catalytic systems enable efficient aerobic oxidations of primary alcohols but they generally show a reduced reactivity in aqueous medium. Herein, we report an oxidative catalytic system composed of Trametes versicolor laccase and TEMPO, which is able to work in buffer solutions at room temperature using ambient air. Although this catalytic system displays great efficiency in aqueous systems, the addition of methyl tert-butyl ether allows the reduction of TEMPO loading, also enhancing the solubility of hydrophobic compounds. This practical methodology promotes the chemoselective aerobic oxidation of hydroxy or amino groups, leading to interesting organic derivatives such as aldehydes, lactones, hemiaminals or lactams.

Silver(I)-Catalyzed deprotection of p -methoxybenzyl ethers: A mild and chemoselective method

The p-methoxybenzyl protecting group (PMB) on various alcohols and an acid was efficiently and selectively cleaved by the action of a catalytic amount of silver(I) hexafluoroantimonate combined with 0.5 equiv of 1,3,5- trimethoxybenzene in dichloromethane at 40 °C.

Mg(ClO4)2-catalyzed intramolecular allylic amination: Application to the total synthesis of demethoxyfumitremorgin C

A Mg(ClO4)2-catalyzed intramolecular amination of allylic alcohols with carbamate or sulfonamide nucleophiles to form substituted piperidine and pyrrolidine derivatives has been developed. This method has been successfully applied to the total synthesis of demethoxyfumitremorgin C.

Biomimetic aerobic oxidation of amino alcohols to lactams

The right path: N-Protected amino alcohols undergo aerobic and biomimetic oxidation to the corresponding lactams in the presence of a ruthenium catalyst and a combination of electron-transfer mediators under air (see scheme). The reaction was used for the synthesis of five-, six-, and seven-, membered lactams and showed good tolerance to a number of N-protecting groups. Copyright

Nucleophilic cycloaromatization of ynamide-terminated enediynes

Introduction of a nitrogen atom at one of the acetylenic termini of 10-, 11-, 12-, and 13-membered benzannulated cyclic enediynes results in a complete suppression of the conventional radical Bergman reaction in favor of a polar cycloaromatization. The latter reaction is catalyzed by acids and proceeds via initial protonation of an ynamide fragment. The resulting ketenimmonium cation then cyclizes to produce naphthyl cation, which rapidly reacts with nucleophiles or undergoes Friedel-Crafts addition to aromatic compounds. In alcohols, addition of the nucleophilic solvent across the activated triple bond competes with the cyclization reaction. The ratio of cyclized to solvolysis products decreases with the increase in ring size.

Hydrogenation of N-acylcarbamates and N-acylsulfonamides catalyzed by a bifunctional [Cp*Ru(PN)] complex

Awakening of the Cp one: the bifunctional complex 1 facilitates the interaction with substrates bearing less electrophilic carbon atoms than ketones, epoxides, and imides. The title reaction was applicable to the reduction of Evans' asymmetric alkylation products to the chiral alcohols along with gtood recovery of the chiral oxazolidinone auxiliary. EWG=electron- withdrawing group.

α-Amidation of cyclic ethers catalyzed by simple copper salt and a mild and efficient preparation method for α,ω-amino alcohols

Copper(II) trifluoromethanesulfonate catalyzed the amidation of cyclic ethers with iminoiodanes under mild conditions (CH2Cl2, 40°C) with good yields (up to 86% based on 97% conversion) and selectivity (only α-amino products were fou