Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C Aliphatic Homoallylic Amines

Wei Sian Li; Ting Shen Kuo; Meng Chi Hsieh; Ming Kang Tsai; Ping Yu Wu; Hsyueh Liang Wu

doi:10.1021/acs.orglett.0c02069

Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C Aliphatic Homoallylic Amines

Wei Sian Li, Ting Shen Kuo, Meng Chi Hsieh, Ming Kang Tsai, Ping Yu Wu, Hsyueh Liang Wu^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

10 引文斯高帕斯（Scopus）

摘要

Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.

原文	英語
頁（從 - 到）	5675-5679
頁數	5
期刊	Organic Letters
卷	22
發行號	14
DOIs	https://doi.org/10.1021/acs.orglett.0c02069
出版狀態	已發佈 - 2020 7月 17

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

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10.1021/acs.orglett.0c02069

其它文件與鏈接

CCDC 1995023: Experimental Crystal Structure Determination
Li, W. (Contributor), Kuo, T. (Contributor), Hsieh, M. (Contributor), Tsai, M. B. (Contributor), Wu, P. (Contributor) & Wu, H. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc24yzlp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc24yzlp&sid=DataCite
資料集: Dataset

引用此

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abstract = "Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.",

author = "Li, {Wei Sian} and Kuo, {Ting Shen} and Hsieh, {Meng Chi} and Tsai, {Ming Kang} and Wu, {Ping Yu} and Wu, {Hsyueh Liang}",

note = "Funding Information: Financial support from the Ministry of Science and Technology of the Republic of China (104-2628-M-003-001-MY3 and 107-2113-M-003-014-MY3) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jul,

day = "17",

doi = "10.1021/acs.orglett.0c02069",

language = "English",

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TY - JOUR

T1 - Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines

T2 - Synthesis of Chiral C Aliphatic Homoallylic Amines

AU - Li, Wei Sian

AU - Kuo, Ting Shen

AU - Hsieh, Meng Chi

AU - Tsai, Ming Kang

AU - Wu, Ping Yu

AU - Wu, Hsyueh Liang

N1 - Funding Information: Financial support from the Ministry of Science and Technology of the Republic of China (104-2628-M-003-001-MY3 and 107-2113-M-003-014-MY3) is gratefully acknowledged. Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/7/17

Y1 - 2020/7/17

N2 - Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.

AB - Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.

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U2 - 10.1021/acs.orglett.0c02069

DO - 10.1021/acs.orglett.0c02069

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

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ER -

Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C Aliphatic Homoallylic Amines

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1995023: Experimental Crystal Structure Determination

引用此