Chemistry–A European Journal

[1, 4]??S??to O??Silyl Migration: Multicomponent Synthesis of α??Thioketones through Chemoselective Transformation of Esters to Ketones with Organolithium Reagents

X Sun, Z Song, H Li, C Sun

Index: Sun, Xianwei; Song, Zhenlei; Li, Hongze; Sun, Changzheng Chemistry - A European Journal, 2013 , vol. 19, # 51 p. 17589 - 17594

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Citation Number: 4

Abstract

Abstract A [1, 4]-S-to O-silyl migration has been exploited to chemoselectively transform esters into ketones by using organolithium reagents, allowing multicomponent synthesis of α- thioketones. Mechanistic studies reveal that this migration proceeds in an intramolecular manner and is more favorable than the corresponding [1, 5]-S-to O-and [1, 3]-C-to O-silyl migrations. The resulting α-thioketones are valuable building blocks for the synthesis of ...