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%).
An Improved Pinacol Rearrangement for the Synthesis of 2-Alkyl-1, 3-Cyclopentanediones
β Scribed by Martinez, Rodolfo A.; Rao, Pemmaraju N.; Kim, Hyun K.
- Book ID
- 120512675
- Publisher
- Taylor and Francis Group
- Year
- 1989
- Tongue
- English
- Weight
- 199 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0039-7911
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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 yi