A Rapid Synthesis of Chiral Allylic Amines via Microwave-assisted Asymmetric Alkenylation of N-Tosyl Aldimines Catalyzed by Rhodium/Chiral Diene Complexes

Balraj Gopula; Hao Wei Zeng; Ping Yu Wu; Julian P. Henschke; Hsyueh Liang Wu

doi:10.1002/jccs.201600888

A Rapid Synthesis of Chiral Allylic Amines via Microwave-assisted Asymmetric Alkenylation of N-Tosyl Aldimines Catalyzed by Rhodium/Chiral Diene Complexes

Balraj Gopula, Hao Wei Zeng, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu

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

6 Scopus citations

Abstract

A method providing expeditious access to chiral allylic amines via a Rh(I)/bicyclo[2.2.1]heptadiene-catalyzed enantioselective alkenylation of N-tosyl aldimines with potassium alkenyltrifluoroborates under microwave irradiation is described. The rate of the asymmetric 1,2-addition reaction, conducted in the presence of 1 mol % of the catalyst, was significantly enhanced as compared to when the standard heating method was applied while still providing the corresponding products without decrease in enantioselectivity.

Original language	English (US)
Pages (from-to)	312-316
Number of pages	5
Journal	Journal of the Chinese Chemical Society
Volume	65
Issue number	3
DOIs	https://doi.org/10.1002/jccs.201600888
State	Published - Mar 2018
Externally published	Yes

Keywords

Chiral allylic amine
Enantioselective
Microwave irradiation

ASJC Scopus subject areas

General Chemistry

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10.1002/jccs.201600888

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title = "A Rapid Synthesis of Chiral Allylic Amines via Microwave-assisted Asymmetric Alkenylation of N-Tosyl Aldimines Catalyzed by Rhodium/Chiral Diene Complexes",

abstract = "A method providing expeditious access to chiral allylic amines via a Rh(I)/bicyclo[2.2.1]heptadiene-catalyzed enantioselective alkenylation of N-tosyl aldimines with potassium alkenyltrifluoroborates under microwave irradiation is described. The rate of the asymmetric 1,2-addition reaction, conducted in the presence of 1 mol % of the catalyst, was significantly enhanced as compared to when the standard heating method was applied while still providing the corresponding products without decrease in enantioselectivity.",

keywords = "Chiral allylic amine, Enantioselective, Microwave irradiation",

author = "Balraj Gopula and Zeng, {Hao Wei} and Wu, {Ping Yu} and Henschke, {Julian P.} and Wu, {Hsyueh Liang}",

note = "Funding Information: Financial support from Ministry of Science and Technology, Republic of China (102-2113-M-003-006-MY2 and 104-2628-M-003-001-MY3), and National Taiwan Normal University is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2017 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = mar,

doi = "10.1002/jccs.201600888",

language = "English (US)",

volume = "65",

pages = "312--316",

journal = "Journal of the Chinese Chemical Society",

issn = "0009-4536",

publisher = "Chinese Chemical Society",

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T1 - A Rapid Synthesis of Chiral Allylic Amines via Microwave-assisted Asymmetric Alkenylation of N-Tosyl Aldimines Catalyzed by Rhodium/Chiral Diene Complexes

AU - Gopula, Balraj

AU - Zeng, Hao Wei

AU - Wu, Ping Yu

AU - Henschke, Julian P.

AU - Wu, Hsyueh Liang

N1 - Funding Information: Financial support from Ministry of Science and Technology, Republic of China (102-2113-M-003-006-MY2 and 104-2628-M-003-001-MY3), and National Taiwan Normal University is gratefully acknowledged. Publisher Copyright: © 2017 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/3

Y1 - 2018/3

N2 - A method providing expeditious access to chiral allylic amines via a Rh(I)/bicyclo[2.2.1]heptadiene-catalyzed enantioselective alkenylation of N-tosyl aldimines with potassium alkenyltrifluoroborates under microwave irradiation is described. The rate of the asymmetric 1,2-addition reaction, conducted in the presence of 1 mol % of the catalyst, was significantly enhanced as compared to when the standard heating method was applied while still providing the corresponding products without decrease in enantioselectivity.

AB - A method providing expeditious access to chiral allylic amines via a Rh(I)/bicyclo[2.2.1]heptadiene-catalyzed enantioselective alkenylation of N-tosyl aldimines with potassium alkenyltrifluoroborates under microwave irradiation is described. The rate of the asymmetric 1,2-addition reaction, conducted in the presence of 1 mol % of the catalyst, was significantly enhanced as compared to when the standard heating method was applied while still providing the corresponding products without decrease in enantioselectivity.

KW - Chiral allylic amine

KW - Enantioselective

KW - Microwave irradiation

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DO - 10.1002/jccs.201600888

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A Rapid Synthesis of Chiral Allylic Amines via Microwave-assisted Asymmetric Alkenylation of N-Tosyl Aldimines Catalyzed by Rhodium/Chiral Diene Complexes

Abstract

Keywords

ASJC Scopus subject areas

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