Metal-Free Radical Annulation-Hydrofunctionalization of 1,6-Enynes for Stereoselective Synthesis of (E)-1-Indanones

Two metal-free radical annulation-hydrofunctionalization cascades of 1,6-enynes have been established, enabling the complete stereoselectivity to access a wide range of functionalized (E)-1-indanones with moderate to good yields. The reaction pathways involve in situ-generated P- or S-centered radic...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 9; no. 7; pp. 1040 - 1044
Main Authors Wu, Ya-Nan, Zhang, Tian-Shu, Hao, Wen-Juan, Tu, Shu-Jiang, Jiang, Bo
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.07.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,7-ENYNES
DESIGN
(E)-1-indanones
RECEPTOR ANTAGONISTS
hydrophosphinylation
radical annulation
FUNCTIONALIZATION
KETONES
BICYCLIZATION CASCADES
LIGANDS
metal-free transformations
INHIBITORS
OXIDES
hydrosulfonylation
CYCLIZATION
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Summary:Two metal-free radical annulation-hydrofunctionalization cascades of 1,6-enynes have been established, enabling the complete stereoselectivity to access a wide range of functionalized (E)-1-indanones with moderate to good yields. The reaction pathways involve in situ-generated P- or S-centered radical-triggered alpha,beta-conjugated addition/5-exo-dig cyclization/H-abstraction sequence, allowing direct and versatile protocols for stereoselective construction of 1-indanone scaffolds with high functional group tolerance and wide substrate scope.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202000197