General scope of 1, 3-dioxolanation of. alpha.,. beta.-unsaturated aldehydes with 1, 2-bis (trimethylsilyloxy) ethane and trimethylsilyl trifluoromethanesulfonate

JR Hwu, LC Leu, JA Robl, DA Anderson…

Index: Hwu, Jih Ru; Leu, Lish-Cheng; Robl, Jeffrey A.; Anderson, Denise A.; Wetzel, John M. Journal of Organic Chemistry, 1987 , vol. 52, # 2 p. 188 - 191

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Citation Number: 52

Abstract

1, 3-Dioxolanation of a, p-unsaturated aldehydes with 1, 2-bis ((trimethylsilyl) oxy) ethane in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst has been systematically investigated. These silylated reagents readily acetalize aliphatic, highly conjugated aliphatic, and aromatic enals. Under the mild, aprotic conditions of the reaction, olefins do not rearrange or isomerize, and the acid-sensitive propionyloxy,(tetrahydropyranyl) oxy, ...