Hydroxy-Assisted Regio- and Stereoselective Synthesis of Functionalized 4-Methylenepyrrolidine Derivatives via Phosphine-Catalyzed [3 + 2] Cycloaddition of Allenoates with <i>o</i>-Hydroxyaryl Azomethine Ylides

Huang, Zhusheng; Bao, Yishu; Zhang, Yu; Yang, Fang; Lü, Tao; Zhou, Qingfa

doi:10.1021/acs.joc.7b02560

Cited by 39 publications

(14 citation statements)

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“…In 2017, Zhou reported the regio- and stereoselective phosphine-catalyzed [3 + 2] cycloadditions of allenoates and o -hydroxyaryl azomethine ylides for the synthesis of functionalized pyrrolidine derivatives (Scheme 292). 363 Under catalysis with 20 mol % of PPh 3 , a wide range of substituted o -hydorxyaryl azomethine ylides reacted with allenoates featuring various straight-chain ester units and bulky ester groups, as well as γ -substituted allenoates, to give the corresponding products in good yields with excellent stereoselectivities. No desired products were formed when α -substituted allenoates were applied in the reaction.…”

Section: Nucleophilic Phosphine Catalysis Of Allenesmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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Section: Nucleophilic Phosphine Catalysis Of Allenesmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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“…In addition, our group also previously studied the synthesize of pyrroline derivatives by azomethine ylides and allenoates under phosphine catalysis or triethylamine. 15 , 16 …”

Section: Introductionmentioning

confidence: 99%

Catalyst-Free [3+2] Cycloaddition of Electron-Deficient Alkynes and o-Hydroxyaryl Azomethine Ylides in Water

Zhu

Xiong

et al. 2020

ACS Omega

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“…Umpolung of azomethine ylides may provide alternative addition/cycloaddition patterns to synthesize chemical entry with structural diversity, which has neither been previously accessible nor required. Very recently, an intramolecular hydrogen bond in the azomethine ylide has shown a huge impact on both reactivity and reaction site of the substrates . Inspired by the above work and our continual interest in phosphine catalysis, we attempted the reaction of o -hydroxyaryl azomethine ylides with MBH carbonates in the presence of phosphine catalyst.…”

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confidence: 99%