Synthesis and some cycloaddition reactions of 2-(triisopropylsilyloxy) acrolein

M Harmata, U Sharma

Index: Harmata, Michael; Sharma, Uday Organic Letters, 2000 , vol. 2, # 17 p. 2703 - 2705

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Citation Number: 39

Abstract

2-(Triisopropylsilyloxy) acrolein is easily prepared by the reaction of triisopropylsilyl triflate and 2-methoxy-2-methyl-[1, 3] dioxan-5-one in the presence of triethylamine. This dienophile reacts with selected dienes in the presence of catalytic amounts of scandium triflate to afford products that are formally 4+ 3 cycloadducts. An exception is seen in the case of butadiene, where only a 4+ 2 cycloadduct is observed.