d⁵‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives

• Main Authors: Dieter Seebach, Manat Pohmakotr, Christian Schregenberger, Beat Weidmann, Raghao S. Mali, Srisuke Pohmakotr
• Other Authors: ETH Zurich
• Format: Article
• Published: 2018
• Subjects: Biochemistry, Genetics and Molecular Biology; Chemical Engineering; Chemistry; Pharmacology, Toxicology and Pharmaceutics
• Online Access: https://repository.li.mahidol.ac.th/handle/123456789/30308
• Institution: Mahidol University

The dienone‐dianion derivatives 1 react with all types of electrophiles tested (alkyl halide, silyl chloride, ester, ketone, aldehyde, epoxide) to give β, γ‐unsaturated carbonyl compounds of type A (see Formulae 2–6, 13, 14 and Tables 1–5). The α‐ and β‐hydroxyalkylation products obtained from 1a–1d...