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Tetrahedron letters

(+)-syn-Benzotriborneol: the first functionalised enantiopure C 3-symmetric benzocyclotrimer

F Fabris, L Bellotto, O De Lucchi

文献索引:Fabris, Fabrizio; Bellotto, Luca; De Lucchi, Ottorino Tetrahedron Letters, 2003 , vol. 44, # 6 p. 1211 - 1213

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被引用次数: 26

摘要

Copper (I) thiophencarboxylate readily and effectively cyclotrimerises protected 5-bromo-6- trimethylstannylborn-5-en-2-ols, leading to oxygen-functionalised benzocyclotrimers. The remarkably high syn to anti ratio is driven by relative displacement of the halide and metal on the alkene moiety and depends on the steric hindrance of the protecting group of the hydroxy function. The less hindered methyl derivative affords exclusively syn- ...