Synthesis of β-Alkoxy Ketones and α′-Functionalized β-Alkoxy Ketones Utilizing Benzotriazole-Stabilized Acyl Anion Synthons

Abstract

1-(α-Alkoxyalkyl)benzotriazoles 1a-d add to phenyl vinyl ether to form key intermediates 4a-d, which readily undergo lithiation and subsequent trapping by a variety of electrophiles to give the expected substituted derivatives 7a-d, 9a-c, 11, 13, 15, and 18 in high yields. Subsequent hydrolysis of these compounds provides a novel high-yield acyl anion synthon approach for the synthesis of β-alkoxy ketones 8 or α′-functionalized β-alkoxy ketones 10, 12, 14, 16, and 19 by short procedures from readily available starting materials.