Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones?
Organic & Biomolecular Chemistry Pub Date: 2022-06-15 DOI: 10.1039/D2OB00854H
Abstract
6-Methylene-5-oxaspiro[2.4]heptanones have been synthesized via base-catalyzed dimerization of available alkynyl cyclopropyl ketones. The reaction proceeds effectively in the presence of the t-BuOK/t-BuOH/THF catalytic system at room temperature to afford the desired spirocycles in a regio- and stereoselective manner. A wider synthetic utility of alkynyl cyclopropyl ketones as novel building blocks was demonstrated by the synthesis of diverse spirocyclopropanes.
Recommended Literature
- [1] An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes Adeline Huiling Loo,Alessandra Bonanni,Martin PumeraAnalyst, 2013,138, 467-471 10.1039/C2AN36199J
- [2] An atlas of endohedral Sc2S cluster fullerenes? Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. FowlerPhys. Chem. Chem. Phys., 2017,19, 419-425 10.1039/C6CP07370K
- [3] An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile? Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo NamDalton Trans., 2016,45, 376-383 10.1039/C5DT04292E
- [4] An intermolecular C–H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines? Christian K. Rank,Alexander W. Jones,Tatjana Wall,Patrick Di Martino-Fumo,Sarah Schr?ck,Markus Gerhards,Frederic W. PatureauChem. Commun., 2019,55, 13749-13752 10.1039/C9CC05240B
- [5] An autonomous self-optimizing flow machine for the synthesis of pyridine–oxazoline (PyOX) ligands? Eric Wimmer,Daniel Cortés-Borda,Solène Brochard,Elvina Barré,Charlotte Truchet,Fran?ois-Xavier FelpinReact. Chem. Eng., 2019,4, 1608-1615 10.1039/C9RE00096H
- [6] An amorphous Cu–In–S nanoparticle-based precursor ink with improved atom economy for CuInSe2 solar cells with 10.85% efficiency? Green Chem., 2017,19, 1268-1277 10.1039/C6GC03280J
- [7] An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay? Suji Lee,Min Su HanChem. Commun., 2021,57, 9450-9453 10.1039/D1CC03638F
- [8] An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes? Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce YeAnalyst, 2021,146, 5542-5549 10.1039/D1AN01071A
- [9] 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
- [10] Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. BudaPhys. Chem. Chem. Phys., 2011,13, 10270-10279 10.1039/C1CP20213H
Journal Name:Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4