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

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journal contribution
posted on 18.02.1998, 00:00 by Alan R. Katritzky, Daming Feng, Ming Qi
1-(α-Alkoxyalkyl)benzotriazoles 1ad add to phenyl vinyl ether to form key intermediates 4ad, which readily undergo lithiation and subsequent trapping by a variety of electrophiles to give the expected substituted derivatives 7ad, 9ac, 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.