Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes
| Autor: | Yong Ho Lee, Bill Morandi, Elliott H. Denton |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Cyclopentenone
Shuffling Chemistry business.industry Intermolecular force chemistry.chemical_element General Chemistry Chemistry Techniques Synthetic Cyclopentanes Modular design 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry Chlorides Alkynes business Palladium |
| Zdroj: | Journal of the American Chemical Society Journal of the American Chemical Society, 142 (50) |
| ISSN: | 0002-7863 1520-5126 |
| DOI: | 10.1021/jacs.0c10832 |
| Popis: | We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an alpha,beta-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy. Journal of the American Chemical Society, 142 (50) ISSN:0002-7863 ISSN:1520-5126 |
| Databáze: | OpenAIRE |
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