Cycloaddition reactions of β-trifluoroacetylvinyl ethers |
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Authors: | Shizheng Zhu Guifang JinWeimin Peng Qichen Huang |
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Affiliation: | a Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China b Department of Chemistry, Peking University, Beijing 100871, People's Republic of China |
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Abstract: | β-Trifluoroacetyl vinyl ethers ROCHCHCOCF3 react smoothly as dienophiles with α,β-unsaturated carbonyl compounds to give the unexpected 2-alkoxyl-5-trifluoroacetyl-3,4-dihydro-2H pyrans. These products are formed by elimination and addition of the alcohol to the products of the normal hetero Diels-Alder reaction (2-alkoxyl-3-trifluoroacetyl-2,3-dihydro-2H pyrans). In contrast, 1,3-dipolar cycloaddition of ROCHCHCOCF3 with ArCHN(O)Me proceeds via a Z-endo transition state to give regio- and stereospecific 4-trifluoroacetyl substituted isoxazolidines and their derivatives. |
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Keywords: | β-trifluoroacetyl vinyl ethers hetero Diels-Alder reaction 1,3-dipolar cycloaddition nitrones trifluoroacetylated isoxazolidines |
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