From Simple to Complex: Rhodium(III)-Catalyzed C–C Bond Cleavage and C–H Bond Functionalization for the Synthesis of 3a,8b-Dihydro-1H-cyclopenta[b]benzofuran-1-ones
| Autor: | Guiyu Guo, Yuanyuan Jia, Wang Zhou, Qijian Jiang, Xiaodong Si, Saihong Wan, Luo Yang |
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| Rok vydání: | 2017 |
| Předmět: |
Annulation
010405 organic chemistry Stereochemistry Organic Chemistry Heteroatom chemistry.chemical_element 010402 general chemistry Triple bond 01 natural sciences Biochemistry Cycloaddition 0104 chemical sciences Rhodium Alpha cleavage chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Benzofuran Bond cleavage |
| Zdroj: | Organic Letters. 19:5026-5029 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b02052 |
| Popis: | A rhodium(III)-catalyzed strategy for the one-step synthesis of polysubstituted cis-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-1-ones from simple 2′-hydroxychalcones and alkynes is developed. This novel transformation involves a sequential C–C bond cleavage and dehydrogenative annulation, leading to the product bearing a quaternary and a tertiary carbon center. 13C labeling experiments revealed that C–C bond cleavage takes place not only at the C–C(C═O) bond but also at the C≡C bond. This study provides an alternative strategy using C–C bond cleavage thus demonstrating the power of this strategy combined with C–H bond functionalization for assembling complex structures from simple starting materials. |
| Databáze: | OpenAIRE |
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