SYNTHETIC ROUTE TO ALPHA-PHOSPHONO-GAMMA-BUTYROLACTONES - SYNTHESIS OF GAMMA-SUBSTITUTED ALPHA-METHYLENE-GAMMA-BUTYROLACTONES

Authors
LEE CW GIL JM OH DY
Citation
Cw. Lee et al., SYNTHETIC ROUTE TO ALPHA-PHOSPHONO-GAMMA-BUTYROLACTONES - SYNTHESIS OF GAMMA-SUBSTITUTED ALPHA-METHYLENE-GAMMA-BUTYROLACTONES, Heterocycles, 45(5), 1997, pp. 943-948
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
5
Year of publication
1997
Pages
943 - 948
Database
ISI
SICI code
0385-5414(1997)45:5<943:SRTA-S>2.0.ZU;2-M
Abstract
Treatment of lithiated homoallylic phosphonates with dimethyl carbamyl chloride gave 2-amidophosphonate derivatives. A solution of 2-amidoph osphonate in DME-H2O (2:1 vol) reacted with 2 eq. iodine at room tempe rature to give pha-phosphono-gamma-iodoalkyl-gamma-butyrolactones in g ood yield, although the products are mixture. Wadsworth-Emmons reactio n of pha-phosphono-gamma-iodoalkyl-gamma-butyrolactones with aldehydes gave kyl)methylene-gamma-iodoalkyl-gamma-butyro-lactone derivatives.