Rhenium-catalyzed regioselective synthesis of phenol derivatives from 1,3-diesters and terminal alkynes

Yoichiro Kuninobu; Takashi Iwanaga; Mitsumi Nishi; Kazuhiko Takai

doi:10.1246/cl.2010.894

Rhenium-catalyzed regioselective synthesis of phenol derivatives from 1,3-diesters and terminal alkynes

Yoichiro Kuninobu, Takashi Iwanaga, Mitsumi Nishi, Kazuhiko Takai

Research output: Contribution to journal › Review article › peer-review

11 Citations (Scopus)

Abstract

Treatment of malonates without a substituent at the active methylene moiety with terminal alkynes gave salicylates regioselectively. In contrast, when malonates bearing a substituent at the active methylene moiety were used, cyclic β-keto esters were generated regioselectively. Treatment of the formed cyclic β-keto esters with In(OTf)₃ gave phenol derivatives via decarboxylation.

Original language	English
Pages (from-to)	894-895
Number of pages	2
Journal	Chemistry Letters
Volume	39
Issue number	8
DOIs	https://doi.org/10.1246/cl.2010.894
Publication status	Published - 2010

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.2010.894

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abstract = "Treatment of malonates without a substituent at the active methylene moiety with terminal alkynes gave salicylates regioselectively. In contrast, when malonates bearing a substituent at the active methylene moiety were used, cyclic β-keto esters were generated regioselectively. Treatment of the formed cyclic β-keto esters with In(OTf)3 gave phenol derivatives via decarboxylation.",

author = "Yoichiro Kuninobu and Takashi Iwanaga and Mitsumi Nishi and Kazuhiko Takai",

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T1 - Rhenium-catalyzed regioselective synthesis of phenol derivatives from 1,3-diesters and terminal alkynes

AU - Kuninobu, Yoichiro

AU - Iwanaga, Takashi

AU - Nishi, Mitsumi

AU - Takai, Kazuhiko

PY - 2010

Y1 - 2010

N2 - Treatment of malonates without a substituent at the active methylene moiety with terminal alkynes gave salicylates regioselectively. In contrast, when malonates bearing a substituent at the active methylene moiety were used, cyclic β-keto esters were generated regioselectively. Treatment of the formed cyclic β-keto esters with In(OTf)3 gave phenol derivatives via decarboxylation.

AB - Treatment of malonates without a substituent at the active methylene moiety with terminal alkynes gave salicylates regioselectively. In contrast, when malonates bearing a substituent at the active methylene moiety were used, cyclic β-keto esters were generated regioselectively. Treatment of the formed cyclic β-keto esters with In(OTf)3 gave phenol derivatives via decarboxylation.

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U2 - 10.1246/cl.2010.894

DO - 10.1246/cl.2010.894

M3 - Review article

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JO - Chemistry Letters

JF - Chemistry Letters

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ER -

Rhenium-catalyzed regioselective synthesis of phenol derivatives from 1,3-diesters and terminal alkynes

Abstract

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