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Synlett 1992; 1992(9): 757-758
DOI: 10.1055/s-1992-21484
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Synthesis and Intramolecular [4+2] Cycloaddition Chemistry of Trienes Tethered with an Ether Linkage

Donald Craig* , John C. Reader
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, England
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Publication Date:
08 March 2002 (online)

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Trienes 4a-d [e.g., methyl 4-(1,1-dimethyl-3,5-hexadienyloxy)crotonate, 4a] have been synthesized via trimethylsilyl trifluoromethanesulfonate mediated reactions of dienophile-derived acetals 2a-d with (E)-1-(trimethylsilyl)-2,4-pentadiene. Thermolysis of 4 gives the corresponding intramolecular cyclo-adducts 5-8 (e.g., methyl 3,3-dimethyl-3,4,4a,7,8,8a-hexahydro-1H-2-benzopyran-8-carboxylate, 5) in excellent yield. The selectivities of the internal [4+2] cycloaddition processes are rationalized in terms of (i) a chair-like conformation of the diene-dienophile linking chain, and (ii) the steric bulk of the phenylsulfonyl group.

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