Synthesis of isoxazolidines via catalyst-free one-pot three-component cycloaddition of sulfoxonium ylides, nitrosoarenes and alkenes

Abstract

A general and practical strategy for the construction of various keto-substituted isoxazolidines via one-pot three-component reaction of easily accessible, safer and more stable sulfoxonium ylides, nitrosoarenes and olefins is described.

Synthesis of 4‐(Trifluoromethyl)‐2,3‐Dihydrothiazoles from α‐Enolic Dithioesters and Imidoyl Sulfoxonium Ylides

“…Water was added to the mixture and subsequent extraction and dryness were conducted. After filtration, the filtrate was evaporated and the resulting residue was purified by silica gel column (eluent: 10% EtOAc in petroleum ether) to give 4-methyl-N-( 1 3,165.6,140.9,139.1,133.4,131.0,129.6 (q,J = 37.3 Hz),128.3,127.2,118.9 (q, J = 268.9 Hz), 112.5 (q, J = 4.4 Hz), 89.1, 21.5; 3, 165.4, 138.9, 136.0, 131.0, 130.7, 130.4, 129.4 (q, J = 37.5 Hz), 128. 7, 128.3, 127.1, 118.9 (q, J = 269.1 Hz), 112.6 (q, J = 4.…”

“…Owing to their bench‐stable and readily available characteristics, they were also performed as the surrogates of diazo compounds to generate carbenes under metal‐catalyzed conditions. It is more fascinating that some transformations of sulfoxonium ylides could be conducted under catalyst‐free and additive‐free conditions [3a–d] . Recently, Cheng's group disclosed a kind of fluorinated imidoyl sulfoxonium ylide and successfully applied it in the synthesis of fluorinated pyrroles [4a] and pyridones, [4b] which demonstrated its potential to synthesize azo‐heterocycles decorated with CF 3 group.…”

“…Among them, sulfoxonium ylides, a useful class of sulfur-containing synthons, were traditionally used to conduct cyclopropanation, epoxidation, aziridination, olefination, and rearrangement reactions. [3,4] Owing to their bench-stable and readily available characteristics, they were also performed as the surrogates of diazo compounds to generate carbenes under metal-catalyzed conditions. It is more fascinating that some transformations of sulfoxonium ylides could be conducted under catalyst-free and additive-free conditions.…”

Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides

“…The mechanism proceeds via nitrone intermediate leading to cycloaddition with styrene (Scheme 70). [74] In the same year, Wang et al also reported a catalyst and oxidant free reaction conditions for the synthesis of isatin hydrozones derivative where sulfoxonium ylide and isatin act as nucleophile and electrophile respectively (Scheme 71). [75]…”

One-pot synthesis of 3-trifluoromethylbenzo[b][1,4]oxazines from CF3-imidoyl sulfoxonium ylides with 2-bromophenols

“…13 In recent years, much attention have been focused on the TM-free insertion reactions of sulfoxonium ylides, which can either be attacked by nucleophiles or attack the electron-deficient center (Scheme 1(c)). 14 Very recently, CF 3 -containing imidoyl sulfoxonium ylides (TFISYs), synthesized for the first time by Cheng's group, were applied in the construction of trifluoromethylpyrroles and trifluoropyridones via TM-free insertion and annulation reactions (Scheme 1(d)). 15 TFISYs as a new kind of important synthon are easily prepared and have been successively employed in the efficient assembly of CF 3 -substituted N-heterocycles, which possess both good stability and high reactivity in comparison with trifluoroacetimidoyl halides and aryl imidoyl sulfoxonium ylides.…”