Oxymercuration-demercuration and hydroboration-oxidation of endo-tricyclo[5.2.2.02,6]undeca-3,8-diene. Stereospecific oxymercuration leading to the 4-exo-hydroxy derivative

Takaishi, Naotake; Fujikura, Yoshiaki; Inamoto, Yoshiaki

doi:10.1021/jo00913a032

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Cited by 23 publications

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“…Substitution of LiEt 3 BH for LiAlH 4 was necessitated by the observation of both substitution and elimination products with LiAlH 4 . This sequence of reactions (Scheme ) gave the endo isomer of compound 2 , a known compound . Catalytic hydrogenation of 2 converted it to another known compound ( 7 ) with six nonequivalent carbons: δ 41.1, 30.0, 28.1, 27.2, 26.6, 20.3.…”

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confidence: 99%

“…19 Subsequent reduction of ketone 6 20 to compound 2 was accomplished via the following three-step sequence: 21 This sequence of reactions (Scheme 2) gave the endo isomer of compound 2, a known compound. 22 Catalytic hydrogenation of 2 converted it to another known compound (7) with six nonequivalent carbons: δ 41.1, 30.0, 28.1, 27.2, 26.6, 20.3. These 13 C NMR chemical shifts match those reported in the literature.…”

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confidence: 99%

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