ALDOL REACTION OF ALLENOLATES GENERATED VIA 1,4-ADDITION OF IODIDE ANION OR ITS EQUIVALENT TO α,β-ACETYLENIC KETONES

Article abstract of DOI:10.1016/S0040-4039(00)85060-1

TMSI, Et2AlI, and (n-Bu)4NI/TiCl4 smoothly added to α,β-acetylenic ketones in a 1,4-fashion to yield allenolates 2, which reacted with aldehydes providing aldol adducts in good overall yield.A high Z-stereoselectivity was achieved by use of (n-Bu)4NI/TiCl4 at -78 deg C, while a high E-stereoselectivity occured at 0 deg C.