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^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

160 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

Y1 - 2016/3/2

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.

UR - https://www.scopus.com/pages/publications/84959420890

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M3 - 文章

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 7

ER -

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

Abstract

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