Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)3/LiI system as the promoter

Chalopin, Thibaut; Jebali, Khaoula; Gaulon‐Nourry, Catherine; Dénès, Fabrice; Lebreton, Jacques; Mathé-Allainmat, Monique

doi:10.1016/j.tet.2015.11.046

Cited by 3 publications

(1 citation statement)

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“…Enynes 2a–2u and the carboxylic acid precursors for the preparation of NHPI esters 1h , 1i , and 1m were synthesized according to previous reports in the literature. − …”

Section: Methodsmentioning

confidence: 99%

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

et al. 2020

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A metal-and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donoraceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. The method provides an operationally simple, robust and stepeconomical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential onepot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches.

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“…Enynes 2a–2u and the carboxylic acid precursors for the preparation of NHPI esters 1h , 1i , and 1m were synthesized according to previous reports in the literature. − …”

Section: Methodsmentioning

confidence: 99%

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

et al. 2020

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ChemInform Abstract: Regioselective Dihydropyran Formation from 4‐Iodo‐2,6‐disubstituted Tetrahydropyran Derivatives Using In(OAc)₃/LiI System as the Promoter.

et al. 2016

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Regioselective Dihydropyran Formation from 4-Iodo-2,6-disubstituted Tetrahydropyran Derivatives Using In(OAc) 3/LiI System as the Promoter. -Starting from 2-substituted homoallyl alcohols and various aldehydes a diastereomeric mixture of 2,6-disubstituted 4-iodotetrahydropyrans is prepared, and the products are further subjected to the regioselective elimination to form dihydropyran derivatives with an ether functionality in position 6. A one-pot two-step version of the reaction sequence is examined. -(CHALOPIN, T.; JEBALI, K.; GAULON-NOURRY, C.; DENES, F.; LEBRETON, J.; MATHE-ALLAINMAT*, M.; Tetrahedron 72 (2016) 2, 318-327, http://dx.

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Six-Membered Ring Systems

Santos¹,

Silva²

2017

Progress in Heterocyclic Chemistry

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Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)3/LiI system as the promoter

Cited by 3 publications

References 38 publications

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

ChemInform Abstract: Regioselective Dihydropyran Formation from 4‐Iodo‐2,6‐disubstituted Tetrahydropyran Derivatives Using In(OAc)₃/LiI System as the Promoter.

Six-Membered Ring Systems

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Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)3/LiI system as the promoter

Cited by 3 publications

References 38 publications

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

ChemInform Abstract: Regioselective Dihydropyran Formation from 4‐Iodo‐2,6‐disubstituted Tetrahydropyran Derivatives Using In(OAc)3/LiI System as the Promoter.

Six-Membered Ring Systems

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ChemInform Abstract: Regioselective Dihydropyran Formation from 4‐Iodo‐2,6‐disubstituted Tetrahydropyran Derivatives Using In(OAc)₃/LiI System as the Promoter.