Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A

Pei Fen Chiang; Wei Sian Li; Jia Hong Jian; Ting Shen Kuo; Ping Yu Wu; Hsyueh Liang Wu

doi:10.1021/acs.orglett.7b03523

Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A

Pei Fen Chiang, Wei Sian Li, Jia Hong Jian, Ting Shen Kuo, 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

27 引文斯高帕斯（Scopus）

摘要

The unprecedented development of asymmetric Rh-catalyzed 1,2-allylation of N-Ts- and N-Ns-aldimines is achieved. This protocol utilizes potassium allyltrifluoroborates and various aldimines to generate enantioenriched homoallylic amines in the presence of 3.0 mol % of Rh(I)/L1b catalyst with up to 90% yield, 98% ee (R = H), and 10:1 diastereoselectivity (R = Me or Ph), yielding the same major diastereomer when using potassium (E)- and (Z)-crotyltrifluoroborate. Its synthetic utility is also illustrated in the total synthesis of (-)-crispine A.

原文	英語
頁（從 - 到）	158-161
頁數	4
期刊	Organic Letters
卷	20
發行號	1
DOIs	https://doi.org/10.1021/acs.orglett.7b03523
出版狀態	已發佈 - 2018 1月 5

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.7b03523

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Link to publication in Scopus

CCDC 1585487: Experimental Crystal Structure Determination
Chiang, P. (Creator), Li, W. (Creator), Jian, J. (Creator), Kuo, T. (Creator), Wu, P. (Creator) & Wu, H. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1q6trh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1q6trh&sid=DataCite
資料集: Dataset
CCDC 1585493: Experimental Crystal Structure Determination
Chiang, P. (Creator), Li, W. (Creator), Jian, J. (Creator), Kuo, T. (Creator), Wu, P. (Creator) & Wu, H. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1q6typ, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1q6typ&sid=DataCite
資料集: Dataset

引用此

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abstract = "The unprecedented development of asymmetric Rh-catalyzed 1,2-allylation of N-Ts- and N-Ns-aldimines is achieved. This protocol utilizes potassium allyltrifluoroborates and various aldimines to generate enantioenriched homoallylic amines in the presence of 3.0 mol % of Rh(I)/L1b catalyst with up to 90% yield, 98% ee (R = H), and 10:1 diastereoselectivity (R = Me or Ph), yielding the same major diastereomer when using potassium (E)- and (Z)-crotyltrifluoroborate. Its synthetic utility is also illustrated in the total synthesis of (-)-crispine A.",

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doi = "10.1021/acs.orglett.7b03523",

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T1 - Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines

T2 - Total Synthesis of (-)-Crispine A

AU - Chiang, Pei Fen

AU - Li, Wei Sian

AU - Jian, Jia Hong

AU - Kuo, Ting Shen

AU - Wu, Ping Yu

AU - Wu, Hsyueh Liang

PY - 2018/1/5

Y1 - 2018/1/5

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AB - The unprecedented development of asymmetric Rh-catalyzed 1,2-allylation of N-Ts- and N-Ns-aldimines is achieved. This protocol utilizes potassium allyltrifluoroborates and various aldimines to generate enantioenriched homoallylic amines in the presence of 3.0 mol % of Rh(I)/L1b catalyst with up to 90% yield, 98% ee (R = H), and 10:1 diastereoselectivity (R = Me or Ph), yielding the same major diastereomer when using potassium (E)- and (Z)-crotyltrifluoroborate. Its synthetic utility is also illustrated in the total synthesis of (-)-crispine A.

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Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A

摘要

ASJC Scopus subject areas

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指紋

資料集

CCDC 1585487: Experimental Crystal Structure Determination

CCDC 1585493: Experimental Crystal Structure Determination

引用此