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 Rh 2(OAc) 4-catalyzed and photo-induced diazo decomposition. The Rh 2(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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