1. Stereoselective Synthesis of Substituted Oxocene Cores by Lewis Acid Promoted Cyclization.
- Author
-
Ghosh AK, Tomaine AJ, and Cantwell KE
- Subjects
- Aldehydes chemistry, Alkenes chemistry, Biological Products chemistry, Catalysis, Cyclization, Magnetic Resonance Spectroscopy, Molecular Structure, Oxocins chemistry, Pyrans chemical synthesis, Stereoisomerism, Lewis Acids chemistry, Oxocins chemical synthesis
- Abstract
Substituted oxocene derivatives have been synthesized by Lewis acid catalyzed reactions of ε-hydroxyalkene 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.
- Published
- 2016
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