SYNTHETIC ROUTE TO ALPHA -PHOSPHONO-GAMMA -BUTYROLACTONES : SYNTHESIS OF GAMMA -SUBSTITUTED ALPHA -METHYLENE-GAMMA -BUTYRO-LACTONES
Treatment of lithiated homoallylic phosphonates with dimethyl carbamyl chloride gave 2-amidophosphonate derivatives. A solution of 2-amidophosphonate in DME-H2O (2:1 vol) reacted with 2 eq. iodine at room temperature to give alpha-phosphono-gamma-iodoalkyl-gamma-butyrolactones in good yield, although the products are mixture. Wadsworth-Emmons reaction of alpha-phosphono-gamma-iodoalkyl-gamma-butyrolactones with aldehydes gave alpha-(alkyl)methylene-gamma-iodoalkyl-gamma-butyro-lactone derivatives.
- Publisher
- Pergamon-Elsevier Science Ltd
- Issue Date
- 1997
- Language
- English
- Article Type
- Article
- Keywords
STEREOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; DERIVATIVES; CARBANION; LACTONES
- Citation
HETEROCYCLES, v.45, no.5, pp.943 - 948
- ISSN
- 0385-5414
- Appears in Collection
- Files in This Item
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