Efficient and chemoselective acetalization and thioacetalization of carbonyls and subsequent deprotection using InF 3 as a reusable catalyst

S Madabhushi, KKR Mallu, N Chinthala, CR Beeram…

Index: Madabhushi, Sridhar; Mallu, Kishore Kumar Reddy; Chinthala, Narsaiah; Beeram, China Ramanaiah; Vangipuram, Venkata Sairam Tetrahedron Letters, 2012 , vol. 53, # 6 p. 697 - 701

Full Text: HTML

Citation Number: 22

Abstract

Acetalization and thioacetalization are important transformations for the protection of a carbonyl group in multistep organic synthesis. Acetals and dithioacetals tolerate a wide range of nucleophilic, basic and organometallic reagents, reducing agents, and nonacidic oxidants. Dithioacetals or dithianes are also useful for the generation of masked carbonyl anions which are employed in a C–C bond formation reaction known as Corey-Seebach reaction. 1 Hence, studies on ...