An Fe(iii)-catalyzed reduction radical tandem strategy to access poly-substituted beta-alkenyl valerolactones

The convenient synthesis of structurally diverse and complex poly-substituted beta-alkenyl valerolactones is first reported via the reduction radical tandem strategy of 2,3-dienoates and allyl alcohols by Fe(iii)-catalysis. Under Fe(iii) catalysis, various allyl alcohols can simultaneously transform...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 6; pp. 1551 - 1556
Main Authors Li, Fu-Yu, Wang, Bei, Xu, Hong, Xiao, Yao, Huang, Dong-Wei, Wang, Ji-Yu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.03.2023
Royal Society of Chemistry
Subjects
Alcohols
Allyl alcohol
Catalysis
Chemistry
Chemistry, Organic
Intermediates
Iron
Organic chemistry
Physical Sciences
Pyrazole
Pyrazoles
Reduction
Science & Technology
Substitutes
VINBLASTINE
ENANTIOSELECTIVE TOTAL-SYNTHESIS
HYDROHYDRAZINATION
CONSTRUCTION
UNACTIVATED ALKENES
OLEFIN HYDROAMINATION
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Summary:The convenient synthesis of structurally diverse and complex poly-substituted beta-alkenyl valerolactones is first reported via the reduction radical tandem strategy of 2,3-dienoates and allyl alcohols by Fe(iii)-catalysis. Under Fe(iii) catalysis, various allyl alcohols can simultaneously transform into alkyl radicals and allyl ester intermediates, which can form products via Michael addition. Interestingly, the method can also prepare spiro-valerolactones and cyclo-valerolactones. In addition, beta-alkenyl valerolactones can be further transformed into unreported pyrazole lactone compounds.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d2qo02038f