A two-step, catalytic synthesis of δ-hydroxy-γ-lactones from allylic acetates and bis (trimethylsilyl) ketene acetals

H Rudler, A Parlier, F Cantagrel, P Harris…

Index: Rudler, Henri; Parlier, Andree; Cantagrel, Frederic; Harris, Paul; Bellassoued, Moncef Chemical Communications, 2000 , # 9 p. 771 - 772

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Citation Number: 11

Abstract

Thus, a mixture of allyl acetate (10 mmol) and bis(trimethylsilyl)ketene acetal 1a† (11 mmol) was heated in THF (70 mL) for 24 h in the presence of Pd(PPh 3 ) 4 (0.2 mmol, 2%). Evaporation of the volatiles, under vacuum, left a residue which was diluted in dichloromethane and filtered through a pad of silica gel. Extraction with aqueous sodium hydroxide followed by acidification and extraction with dichloromethane gave a mixture of acids. After cooling the solution to ...