Premium
Synthesis of Spirocycles via Ni‐Catalyzed Intramolecular Coupling of Thioesters and Olefins
Author(s) -
Liu Wenfei,
Xu Wenhua,
Wang Juanjuan,
Lu Hong,
Xu PengFei,
Wei Hao
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100390
Subject(s) - intramolecular force , substituent , decarbonylation , chemistry , alkene , olefin fiber , combinatorial chemistry , thioester , thiol , catalysis , organic chemistry , enzyme
A nickel‐catalyzed intramolecular coupling of thioesters and olefins has been developed for the efficient synthesis of spirocycles, a privileged scaffold commonly found in natural products. This transformation is characterized by the simultaneous transfer of both acyl and thiol moieties to the alkene, with the suppression of decarbonylation and β‐hydrogen elimination. Initial mechanistic investigations are consistent with an oxidative addition/olefin insertion/reductive elimination mechanism. The incorporated methylene sulfide substituent can undergo a variety of further reactions to increase molecular diversity and complexity. These results demonstrate that thioester derivatives can be used as powerful building blocks for the assembly of complex scaffolds.