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Iron(III) Chloride/Phenylsilane‐Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly‐Substituted γ‐Butyrolactones
Author(s) -
Zhang Hua,
Zhan XiaoYu,
Chen XuLing,
Tang Lei,
He Shuai,
Shi ZhiChuan,
Wang Yu,
Wang JiYu
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900843
Subject(s) - chemistry , tetrahydrofuran , phenylsilane , alkyl , allyl chloride , intramolecular force , allyl alcohol , radical , cascade reaction , catalysis , maleimide , medicinal chemistry , radical initiator , organic chemistry , polymerization , polymer , solvent
A iron‐catalyzed free radical cascade reaction of allyl alcohols with N‐substituted maleimides for accessing poly‐substituted γ‐butyrolactones has been developed. In this protocol, various allyl alcohols can open N‐substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ‐butyrolactones. In this protocol, spiro γ‐butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram‐scale.