Chiral cobalt(<scp>ii</scp>) complex-promoted asymmetric <i>para</i>-Claisen rearrangement of allyl α-naphthol ethers

Zeng, Hongkun; Wang, Lifeng; Su, Zhishan; Ying, Meijia; Lin, Lili; Feng, Xiaoming

doi:10.1039/d3sc05677e

Chem. Sci.

2023

DOI: 10.1039/d3sc05677e

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Chiral cobalt(ii) complex-promoted asymmetric para-Claisen rearrangement of allyl α-naphthol ethers

Hongkun Zeng,

Lifeng Wang,

Zhishan Su

et al.

Abstract: A highly enantioselective para-Claisen rearrangement of allyl α-naphthol ethers is realized by a chiral cobalt(ii)/N,N′-dioxide complex catalyst.

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2024

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Cited by 3 publications

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Tosylhydrazide-Induced 1,6-Enyne Radical Cyclization under Copper Catalysis: Access to 3,4-Dihydronaphthalen-1(2H)-one Derivatives

Hosseini Nasab,

Rajai-Daryasarei,

Rominger

et al. 2024

J. Org. Chem.

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We describe an approach to access 4-aroyl-3-aryl-3,4dihydronaphthalen-1(2H)-one derivatives in 41−79% yields through the Cu-catalyzed radical cyclization/desulfonylation of 1,6-enynes with tosylhydrazide under air conditions. This alternative desulfonylation strategy combines mild conditions, external oxidant-free processes, and sustainability, contributing to more environmentally friendly organic synthesis. The mechanistic studies showed that the CuCl/O 2 combination serves as the source of the oxygen atom needed to form the C�O bond. The existence of tosylhydrazide is crucial for this conversion.

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Tosylhydrazide-Induced 1,6-Enyne Radical Cyclization under Copper Catalysis: Access to 3,4-Dihydronaphthalen-1(2H)-one Derivatives

Hosseini Nasab,

Rajai-Daryasarei,

Rominger

et al. 2024

J. Org. Chem.

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Asymmetric dearomatization of benzyl 1-naphthyl ethers via [1,3] O-to-C rearrangement

Zeng,

Wen,

Lin

et al. 2024

Chem. Commun.

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Rearrangement reactions: Important tool for the synthesis of piperazines

Sharma,

Kumar,

Mazumder

et al. 2024

Synthetic Communications

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Chiral cobalt(ii) complex-promoted asymmetric para-Claisen rearrangement of allyl α-naphthol ethers

Abstract: A highly enantioselective para-Claisen rearrangement of allyl α-naphthol ethers is realized by a chiral cobalt(ii)/N,N′-dioxide complex catalyst.

Cited by 3 publications

References 74 publications

Tosylhydrazide-Induced 1,6-Enyne Radical Cyclization under Copper Catalysis: Access to 3,4-Dihydronaphthalen-1(2H)-one Derivatives

Tosylhydrazide-Induced 1,6-Enyne Radical Cyclization under Copper Catalysis: Access to 3,4-Dihydronaphthalen-1(2H)-one Derivatives

Asymmetric dearomatization of benzyl 1-naphthyl ethers via [1,3] O-to-C rearrangement

Rearrangement reactions: Important tool for the synthesis of piperazines

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