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

Citation
M. Harmata et U. Sharma, Synthesis and some cycloaddition reactions of 2-(triisopropylsilyloxy)acrolein, ORG LETT, 2(17), 2000, pp. 2703-2705
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
17
Year of publication
2000
Pages
2703 - 2705
Database
ISI
SICI code
1523-7060(20000824)2:17<2703:SASCRO>2.0.ZU;2-9
Abstract
[GRAPHICS] 2-(Triisopropylsilyloxy)acrolein is easily prepared by the reaction of trii sopropylsilyl triflate and 2-methoxy-2-methyl-[1,3]dioxan-5-one in the pres ence of triethylamine. This dienophile reacts with selected dienes in the p resence of catalytic amounts of scandium triflate to afford products that a re formally 4 + 3 cycloadducts. An exception is seen in the case of butadie ne, where only a 4 + 2 cycloadduct is observed.