Methodologies for 2-alkylidene-1,3-cyclopentanediones
β Scribed by Philip E. Eaton; William H. Bunnelle
- Book ID
- 104242328
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 209 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Methods for the synthesis of 2-alkylidene-1,3-cyclopentanediones are given along withe preliminary information on the reactivity of these ene-diones. Simple 2-alkylidene-1,3-cyclopentanediones are little known. Singular examples in which the exocyclic double bond is stabilized by heteroatom substitution or by conjugation with aromatic or extended systems have been mentioned; 1.
simpler "stripped down 'I derivatives of this ene-dione system are exceedingly rare.
π SIMILAR VOLUMES
Direct ketalization of 2-methyl-1,3-cyclopentanedione 3 led to the corresponding diethylene ketal 2. Carefully controlled hydrolysis of compound 2 afforded the monoethylene ketal 1 in high yield.
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%).