Stereoselective Synthesis of Substituted Oxocene Cores by Lewis Acid Promoted Cyclization
| Autor: | Arun K. Ghosh, Kelsey E. Cantwell, Anthony J. Tomaine |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Magnetic Resonance Spectroscopy
Dihydropyran Stereoisomerism Alkenes 010402 general chemistry 01 natural sciences Biochemistry Catalysis Article chemistry.chemical_compound Organic chemistry Lewis acids and bases Physical and Theoretical Chemistry Lewis Acids Pyrans Aldehydes Biological Products Olefin fiber Molecular Structure 010405 organic chemistry Oxocins Organic Chemistry Nuclear magnetic resonance spectroscopy Prins reaction 0104 chemical sciences chemistry Cyclization Stereoselectivity |
| Zdroj: | Organic Letters. 18:396-399 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.5b03411 |
| Popis: | Substituted oxocene derivatives have been synthesized by Lewis acid catalyzed reactions of ε-hydroxy-alkene and substituted aromatic aldehydes. The Cu(OTf)2-bis-phosphine catalyzed reaction typically provides substituted dihydropyran derivatives through an olefin-migration, followed by a Prins cyclization. The corresponding reaction catalyzed by TMSOTf or BF3·OEt2 provided eight-membered cyclic ethers, oxocenes, selectively. This methodology provides convenient access to a variety of 2,4,8-trisubstituted oxocenes in good yields and excellent diastereoselectivities. |
| Databáze: | OpenAIRE |
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