✦ LIBER ✦

Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones. Part 3: Oxidative ring cleavage of 3-hydroxyethyl-1,2-cyclopentanediones: synthesis of α-hydroxy-γ-lactone acids and spiro-γ-dilactones

✍ Scribed by Anne Paju; Tõnis Kanger; Olivia Niitsoo; Tõnis Pehk; Aleksander-Mati Müürisepp; Margus Lopp

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 245 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00452-x

No coin nor oath required. For personal study only.

✦ Synopsis

A Ti(OiPr) 4 /diethyl tartrate/tBuOOH complex oxidizes 3-hydroxyethyl-1,2-cyclopentanediones, resulting in hydroxylated/ring cleavage products-lactone acids of high enantioselectivity (up to 95% ee) with good yields (up to 75%). These compounds are converted into chiral spiro-g-dilactones in good yield.

📜 SIMILAR VOLUMES

Asymmetric oxidation of 3-alkyl-1,2-cycl

Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones. Part 2: Oxidative ring cleavage of 3-alkyl-1,2-cyclopentanediones: synthesis of 2-alkyl-γ-lactone acids

✍ Anne Paju; Tõnis Kanger; Tõnis Pehk; Rasmus Lindmaa; Aleksander-Mati Müürisepp; 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 308 KB

Ti(OiPr) 4 /diethyl tartrate/tBuOOH system oxidizes 3-alkyl-1,2-cyclopentanediones resulting in hydroxylated ring cleavage products 2-alkyl-g-lactone acids, in high enantioselectivity ( 95% ee) and satisfactory isolated yields (up to 55%).