Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives |
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Authors: | Duan Shaofeng Cress Karen Waynant Kris Ramos-Miranda Elias Herndon James W |
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Institution: | Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003-8001, USA |
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Abstract: | Fluoride-based deprotection of silylated 2-alkynylbenzyl alcohol derivatives featuring carbonyl-substituted alkynes results in the direct synthesis of alkylidenephthalan vinylogous esters. The reaction is selective for the Z alkylidenephthalans in a thermodynamically controlled process. Similar compounds are also produced in the coupling of Fischer carbene complexes with 2-alkynylbenzoyl derivatives in an aqueous solvent system. Subsequent acid-catalyzed inter- or intramolecular Diels-Alder reactions lead to hydronaphthalene or hydrophenanthrene derivatives. |
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