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Synthesis of Spirocycles via Ni-Catalyzed Intramolecular Coupling of Thioesters and Olefins |
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| Authors: | Wenfei Liu Dr. Wenhua Xu Juanjuan Wang Dr. Hong Lu Prof. Dr. Peng-Fei Xu Prof. Dr. Hao Wei |
| Affiliation: | 1. Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710069 P. R. China These authors contributed equally to this work.;2. Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710069 P. R. China;3. Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 P. R. China |
| Abstract: | 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. |
| Keywords: | addition reaction cut-and-sew reactions nickel spiro compound thioesters |