Preparation of α-Methylene-γ-butyrolactones with Difluoromethylene Functionalities. -The key to the preparation of title compounds such as (XII), of interest as pharmaceutical drugs, is the regioselective reduction of the ester group of compound (VI) activated with a difluoromethylene unit to give
Preparation and reactivity of an α-(difluoromethylene)-γ-lactone
✍ Scribed by Minoru Suda
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 179 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
3-(Difluoromethylene)-4,4-dimethyloxolan-2-one, prepared by difluoromethylenation of 4,4-dimethyloxolan-2,3-dione, exhibits marked reactivity toward nucleophilic reagents. a-Methylene-y-lactone structure is found in many naturally occurring terpenes and some of them are known to exhibit biological activities. Encouraged by this nature, a large number of synthetic m,ethods to construct this unique functional moiety have been developed by now. 1) As a part of our
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Sulfination of brorrrodifluoroacetate or acetaitiide 1 with sodiurrr dithionite gives the corresponding sulfinates 2a and 2b, respectively, which upon cuprous bromide catalyzed allylation afford the allylsulfonyldifluoroacetate and acetatnides. Phenyl-or alkylsulfonyldifluoroacetates and acetamides