Stereoselective sulfenylation of oxindole-derived propargyl alcohols to access sulfenylated-3-alkenyloxindoles?
Organic & Biomolecular Chemistry Pub Date: 2021-11-12 DOI: 10.1039/D1OB01921J
Abstract
A Ca-catalyzed, tetrasubstituted alkenyl-sulfenylation was achieved using readily available aryl/alkyl thiols and easily prepared oxindole-derived propargyl alcohols under solvent-free conditions. The reaction proceeded with hydrogen bonding assisted regioselective α-thiolation and subsequent calcium catalyzed stereoselective alkenylation to yield E-alkenyl thioethers with high diastereoselectivity.
Recommended Literature
- [1] An approach to the structure and vibrational analysis of cis- and trans-3-chlorostyrene through IR/Raman and INS spectroscopies and theoretical ab initio/DFT calculations? J. M. Granadino-Roldán,M. Fernández-Gómez,A. Navarro,T. Pe?a Ruiz,U. A. JayasooriyaPhys. Chem. Chem. Phys., 2004,6, 1133-1143 10.1039/B314243D
- [2] An apparatus for determining small amounts of alchohol in sour milk and urine Analyst, 1964,89, 272-275 10.1039/AN9648900272
- [3] An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment? Xin Fu,Qing-rong Liang,Rong-guang Luo,Yan-shu Li,Xiao-ping Xiao,Lu-lu Yu,Wen-zhe Shan,Guang-qin FanJ. Mater. Chem. B, 2019,7, 3088-3099 10.1039/C9TB00349E
- [4] Aggregation behaviour of biocompatible choline carboxylate ionic liquids and their interactions with biomolecules through experimental and theoretical investigations? Somenath Panda,Kaushik Kundu,Anusha Basaiahgari,Sanjib Senapati,Ramesh L. GardasNew J. Chem., 2018,42, 7105-7118 10.1039/C8NJ00336J
- [5] An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins? Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois MatheyDalton Trans., 2019,48, 5523-5526 10.1039/C9DT00838A
- [6] An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction? Sandip Gangadhar Balwe,Yeon Tae JeongOrg. Biomol. Chem., 2018,16, 1287-1296 10.1039/C7OB02933K
- [7] An analysis of the WTC fires using CIB correlations and simple modeling JGQuintiere 10.1177/0734904121989670
- [8] An ion-exchange method for determining paraquat residues in food crops Analyst, 1965,90, 99-106 10.1039/AN9659000099
- [9] Alternative synthesis of the anti-baldness compound RU58841? RSC Adv., 2014,4, 14143-14148 10.1039/C4RA00332B
- [10] Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz JaremkoRSC Adv., 2020,10, 215-227 10.1039/C9RA09350H
Journal Name:Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4