The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes

Jian Jun Feng; Tao Yan Lin; Chao Ze Zhu; Huamin Wang; Hai Hong Wu; Junliang Zhang

doi:10.1021/jacs.6b00386

The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes

Jian Jun Feng, Tao Yan Lin, Chao Ze Zhu, Huamin Wang, Hai Hong Wu, Junliang Zhang

School of Chemistry and Molecular Engineering

East China Normal University

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

157 Scopus citations

Abstract

Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)₂]BF₄ as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst was changed to [Rh(η⁶-C₁₀H₈) (COD)]SbF₆, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.

Original language	English
Pages (from-to)	2178-2181
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	7
DOIs	https://doi.org/10.1021/jacs.6b00386
State	Published - 2 Mar 2016

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title = "The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes",

abstract = "Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)2]BF4 as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst was changed to [Rh(η6-C10H8) (COD)]SbF6, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.",

author = "Feng, \{Jian Jun\} and Lin, \{Tao Yan\} and Zhu, \{Chao Ze\} and Huamin Wang and Wu, \{Hai Hong\} and Junliang Zhang",

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doi = "10.1021/jacs.6b00386",

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T1 - The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes

AU - Feng, Jian Jun

AU - Lin, Tao Yan

AU - Zhu, Chao Ze

AU - Wang, Huamin

AU - Wu, Hai Hong

AU - Zhang, Junliang

PY - 2016/3/2

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N2 - Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)2]BF4 as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst was changed to [Rh(η6-C10H8) (COD)]SbF6, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.

AB - Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)2]BF4 as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst was changed to [Rh(η6-C10H8) (COD)]SbF6, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.

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IS - 7

ER -

The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes

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