2-Alkenyl-Substituted Methyl 2-Siloxycyclopropanecarboxylates as Masked Vinyl Ketones: Efficient Syntheses of Highly Functionalized Michael Adducts.

Article abstract of DOI:10.1021/jo00350a022

2-Alkenyl-substituted methyl 2-siloxycyclopropanecarboxylates 3a, 3b, and 6 - easily available from the corresponding silyl enol ether - react with a variety of O-, N-, S-, and C-nucleophiles under mild acidic or basic conditions providing polyfunctionalized products 7-19 in good to excellent yields via 1,4-addition to vinyl ketones formed in situ.Due to the versatility of the nitro group, nitroalakne, adducts 15-19 are of special interest for further transformations.