Ruthenium-catalyzed reactions of acyclic α,β-enones with olefins and their reaction mechanisms

Taisuke Sato; Fumitoshi Kakiuchi; Naoto Chatani; Shinji Murai

doi:10.1246/cl.1998.893

Ruthenium-catalyzed reactions of acyclic α,β-enones with olefins and their reaction mechanisms

Taisuke Sato, Fumitoshi Kakiuchi, Naoto Chatani, Shinji Murai

Research output: Contribution to journal › Article › peer-review

64 Citations (Scopus)

Abstract

The reaction of 4,4-dimethyl-5-phenyl-4-peneten-3-one with styrene (2) using Ru(H)₂(CO)(PPh₃)₃ as the catalyst gave the stereochemically retained product. In the case of 2,2-dimethyl-4-hexen-3-one, the stereochemically inverted branched product was obtained. These results are consistent with two different reaction pathways operating, i.e. one involving a direct C-H bond cleavage and the other, a pathway involving hydrometallation.

Original language	English
Pages (from-to)	893-894
Number of pages	2
Journal	Chemistry Letters
Issue number	9
DOIs	https://doi.org/10.1246/cl.1998.893
Publication status	Published - 1998 Jan 1
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.1998.893

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abstract = "The reaction of 4,4-dimethyl-5-phenyl-4-peneten-3-one with styrene (2) using Ru(H)2(CO)(PPh3)3 as the catalyst gave the stereochemically retained product. In the case of 2,2-dimethyl-4-hexen-3-one, the stereochemically inverted branched product was obtained. These results are consistent with two different reaction pathways operating, i.e. one involving a direct C-H bond cleavage and the other, a pathway involving hydrometallation.",

author = "Taisuke Sato and Fumitoshi Kakiuchi and Naoto Chatani and Shinji Murai",

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AU - Sato, Taisuke

AU - Kakiuchi, Fumitoshi

AU - Chatani, Naoto

AU - Murai, Shinji

PY - 1998/1/1

Y1 - 1998/1/1

N2 - The reaction of 4,4-dimethyl-5-phenyl-4-peneten-3-one with styrene (2) using Ru(H)2(CO)(PPh3)3 as the catalyst gave the stereochemically retained product. In the case of 2,2-dimethyl-4-hexen-3-one, the stereochemically inverted branched product was obtained. These results are consistent with two different reaction pathways operating, i.e. one involving a direct C-H bond cleavage and the other, a pathway involving hydrometallation.

AB - The reaction of 4,4-dimethyl-5-phenyl-4-peneten-3-one with styrene (2) using Ru(H)2(CO)(PPh3)3 as the catalyst gave the stereochemically retained product. In the case of 2,2-dimethyl-4-hexen-3-one, the stereochemically inverted branched product was obtained. These results are consistent with two different reaction pathways operating, i.e. one involving a direct C-H bond cleavage and the other, a pathway involving hydrometallation.

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Ruthenium-catalyzed reactions of acyclic α,β-enones with olefins and their reaction mechanisms

Abstract

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