Photoaddition Reactions of Acetylpyridines with Silyl Ketene Acetals: SET vs [2+ 2]-Cycloaddition Pathways

…, HY Lee, DW Cho, DW Cho, PS Mariano

Index: Cho, Dae Won; Park, Hea Jung; Yoon, Ung Chan; Lee, Hyang-Yeol; Mariano, Patrick S. Journal of Organic Chemistry, 2012 , vol. 77, # 22 p. 10304 - 10313

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Citation Number: 7

Abstract

Photoaddition reactions of silyl ketene acetals with 2-, 3-and 4-acetylpyridine have been explored. The results show that the acetylpyridines react with an electron rich, dimethyl- substituted silyl ketene acetal via a pathway in which excited state single electron transfer (SET) takes place to produce β-hydroxyesters in high yields. In contrast, photochemical reactions of the acetylpyridines with an electron deficient, nonmethyl-substituted silyl ...