Copper-Catalyzed Cascade Annulation of Malonate-Tethered <i>O</i>-Acyl Oximes with Cyclic 1,3-Dicarbonyl Compounds for the Synthesis of Spiro-Pentacyclic Derivatives.

Wang K; Guan HR; Ren WL; Yang HT; Miao CB

doi:10.1021/acs.joc.1c01122

Copper-Catalyzed Cascade Annulation of Malonate-Tethered O-Acyl Oximes with Cyclic 1,3-Dicarbonyl Compounds for the Synthesis of Spiro-Pentacyclic Derivatives.

Affiliations

1. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.
Authors
Wang K¹
Guan HR¹
Ren WL¹
Yang HT¹
Miao CB¹
(5 authors)

ORCIDs linked to this article

The Journal of Organic Chemistry, 09 Aug 2021, 86(17):12309-12317
https://doi.org/10.1021/acs.joc.1c01122 PMID: 34369761

Abstract

A copper-catalyzed cascade annulation of malonate-tethered O-acyl oximes with cyclic 1,3-dicarbonyl compounds has been developed for the rapid synthesis of spiro-pentacyclic derivatives. This reaction allows the one-step formation of five C-C/N/O bonds and an angular tricyclic core under very mild conditions and shows excellent regioselectivity and stereoselectivity.

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Copper-catalyzed [1,3]-nitrogen rearrangement of O-aryl ketoximes via oxidative addition of N-O bond in inverse electron flow.
Suzuki M, Terada M, Nakamura I
Chem Sci, 14(21):5705-5711, 01 May 2023
Cited by: 1 article | PMID: 37265725 | PMCID: PMC10231427
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Funders who supported this work.

Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University (1)

Grant ID: CJ20200087
2 publications

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology (1)

Grant ID: BM2012110
46 publications

Jiangsu Province Key Laboratory of Fine Petrochemical Engineering (1)

Grant ID: KF2001
1 publication

Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (1)

Grant ID: 19KJB150002
3 publications

Natural Science Foundation of Jiangsu Province (1)

Grant ID: BK20181462
7 publications

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Copper-Catalyzed Cascade Annulation of Malonate-Tethered O-Acyl Oximes with Cyclic 1,3-Dicarbonyl Compounds for the Synthesis of Spiro-Pentacyclic Derivatives.

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Copper-catalyzed [1,3]-nitrogen rearrangement of O-aryl ketoximes via oxidative addition of N-O bond in inverse electron flow.

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Funding

Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University (1)

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology (1)

Jiangsu Province Key Laboratory of Fine Petrochemical Engineering (1)

Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (1)

Natural Science Foundation of Jiangsu Province (1)

Partnerships & funding

Search life-sciences literature (45,103,589 articles, preprints and more)

Copper-Catalyzed Cascade Annulation of Malonate-Tethered O-Acyl Oximes with Cyclic 1,3-Dicarbonyl Compounds for the Synthesis of Spiro-Pentacyclic Derivatives.

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Affiliations

Authors

ORCIDs linked to this article

Abstract

Full text links

Citations & impact

Impact metrics

Article citations

Copper-catalyzed [1,3]-nitrogen rearrangement of O-aryl ketoximes via oxidative addition of N-O bond in inverse electron flow.

Similar Articles

Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins.

Copper-Catalyzed Bisannulations of Malonate-Tethered O-Acyl Oximes with Pyridine, Pyrazine, Pyridazine, and Quinoline Derivatives for the Construction of Dihydroindolizine-Fused Pyrrolidinones and Analogues.

NHC-Catalyzed Generation of α,β-Unsaturated Acylazoliums for the Enantioselective Synthesis of Heterocycles and Carbocycles.

Copper-Catalyzed Annulation of O-Acyl Oximes with Cyclic 1,3-Diones for the Synthesis of 7,8-Dihydroindolizin-5(6H)-ones and Cyclohexanone-Fused Furans.

Funding

Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University (1)﻿

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology (1)﻿

Jiangsu Province Key Laboratory of Fine Petrochemical Engineering (1)﻿

Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (1)﻿

Natural Science Foundation of Jiangsu Province (1)﻿

Partnerships & funding

Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University (1)

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology (1)

Jiangsu Province Key Laboratory of Fine Petrochemical Engineering (1)

Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (1)

Natural Science Foundation of Jiangsu Province (1)