A detachable ester bond enables perfect Z-alkylations of olefins for the synthesis of tri- and tetrasubstituted alkenesElectronic supplementary information (ESI) available. See DOI: 10.1039/c5cc03474d
2-Vinyl-substituted phenol and an alpha-bromoester undergo a tandem esterification-alkylation reaction in the presence of a Cu-amine catalyst system to produce benzene-fused lactone. Z -Alkylated styrene is obtained after hydrolysis of the lactone with perfect selectivity. The simple protocol develo...
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| creator | Nishikata, Takashi Nakamura, Kimiaki Inoue, Yuki Ishikawa, Shingo |
| description | 2-Vinyl-substituted phenol and an alpha-bromoester undergo a tandem esterification-alkylation reaction in the presence of a Cu-amine catalyst system to produce benzene-fused lactone.
Z
-Alkylated styrene is obtained after hydrolysis of the lactone with perfect selectivity. The simple protocol developed in this work opens a new avenue in the multi-substitution chemistry of alkenes.
We developed a tandem esterification-intramolecular alkylation reaction catalyzed by a copper catalyst, leading to the formation of a lactone, followed by hydrolysis of the resulting lactone to give
Z
-alkylated alkenes in good yields with perfect selectivities. |
| doi_str_mv | 10.1039/c5cc03474d |
| format | Article |
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Z
-Alkylated styrene is obtained after hydrolysis of the lactone with perfect selectivity. The simple protocol developed in this work opens a new avenue in the multi-substitution chemistry of alkenes.
We developed a tandem esterification-intramolecular alkylation reaction catalyzed by a copper catalyst, leading to the formation of a lactone, followed by hydrolysis of the resulting lactone to give
Z
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Z
-Alkylated styrene is obtained after hydrolysis of the lactone with perfect selectivity. The simple protocol developed in this work opens a new avenue in the multi-substitution chemistry of alkenes.
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Z
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Z
-Alkylated styrene is obtained after hydrolysis of the lactone with perfect selectivity. The simple protocol developed in this work opens a new avenue in the multi-substitution chemistry of alkenes.
We developed a tandem esterification-intramolecular alkylation reaction catalyzed by a copper catalyst, leading to the formation of a lactone, followed by hydrolysis of the resulting lactone to give
Z
-alkylated alkenes in good yields with perfect selectivities.</abstract><doi>10.1039/c5cc03474d</doi><tpages>4</tpages></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | A detachable ester bond enables perfect Z-alkylations of olefins for the synthesis of tri- and tetrasubstituted alkenesElectronic supplementary information (ESI) available. See DOI: 10.1039/c5cc03474d |
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