A new route for generation of alpha-lambda3-iodanyl ketones via ester exchange of (Z)-(beta-acetoxyvinyl)-lambda3-iodanes: their nucleophilic substitutions with halides and sulfur and phosphorus nucleophiles.
An efficient method for generation of alpha-lambda3-iodanyl ketones from (Z)-(2-acetoxyvinyl)(phenyl)-lambda3-iodanes was developed. The method involves ester exchange of (Z)-2-acetoxyvinyl-lambda3-iodanes with methanol in the presence of triethylamine. alpha-lambda3-Iodanyl ketones react with a variety of nucleophiles such as halides, thiols, phosphines, phosphinic acids, and phosphates, under the conditions which produce alpha-functionalized carbonyl compounds probably via an S(N)2 pathway.
Ochiai
Masahito
M
Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph2.tokushima-u.ac.jp
Nishitani
Junichi
J
Nishi
Yoshio
Y