Rhodium(I)-Catalyzed Cyclization of Allenynes with a Carbonyl Group through Unusual Insertion of a CO Bond into a Rhodacycle Intermediate

Rhodium(I)-Catalyzed Cyclization of Allenynes with a Carbonyl Group through Unusual Insertion of a CO Bond into a Rhodacycle Intermediate

Rhodium(I)-catalyzed cyclization of allenynes with a tethered carbonyl group was investigated. An unusual insertion of a CO bond into the C(sp2)-rhodium bond of a rhodacycle intermediate occurs via a highly strained transition state. Direct reductive elimination from the obtained rhodacyle intermedi...

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Veröffentlicht in:Angewandte Chemie 2014-01, Vol.126 (4), p.1153
Hauptverfasser: Oonishi, Yoshihiro, Yokoe, Takayuki, Hosotani, Akihito, Sato, Yoshihiro
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creator Oonishi, Yoshihiro
Yokoe, Takayuki
Hosotani, Akihito
Sato, Yoshihiro
description Rhodium(I)-catalyzed cyclization of allenynes with a tethered carbonyl group was investigated. An unusual insertion of a CO bond into the C(sp2)-rhodium bond of a rhodacycle intermediate occurs via a highly strained transition state. Direct reductive elimination from the obtained rhodacyle intermediate proceeds to give a tricyclic product containing an 8-oxabicyclo[3.2.1]octane skeleton, while [beta]-hydride elimination from the same intermediate gives products that contain fused five- and seven-membered rings in high yields.
doi_str_mv 10.1002/ange.201308824
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title Rhodium(I)-Catalyzed Cyclization of Allenynes with a Carbonyl Group through Unusual Insertion of a CO Bond into a Rhodacycle Intermediate
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