Synthesis of oxygen-containing heterocyclic compounds based on the intramolecular O-H insertion and Wolff rearrangement of α-diazocarbonyl compounds |
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| Authors: | Mingyi Liao |
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| Institution: | Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China |
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| Abstract: | The addition products of Ti(IV)-enolate derived from β-keto α-diazo carbonyl compound to ketones or α,β-unsaturated compounds were subjected to Rh2(OAc)4-catalyzed and photo-induced diazo decomposition. The Rh2(OAc)4-catalyzed reaction afforded intramolecular O-H insertion products, while the photo-induced reaction gave Wolff rearrangement/intramolecular nucleophilic addition products. The transformations represent new approaches to tetrahydrofuran and γ-butyrolactone derivatives. |
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| Keywords: | Diazo compounds Rh(II) carbene Wolff rearrangement Tetrahydrofuran derivative γ-butyrolactone derivative |
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