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
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

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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 = "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",

volume = "65",

pages = "312--316",

journal = "Journal of the Chinese Chemical Society",

issn = "0009-4536",

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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

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

UR - https://www.scopus.com/pages/publications/85020716528

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DO - 10.1002/jccs.201600888

M3 - Article

AN - SCOPUS:85020716528

SN - 0009-4536

VL - 65

SP - 312

EP - 316

JO - Journal of the Chinese Chemical Society

JF - Journal of the Chinese Chemical Society

IS - 3

ER -

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

Abstract

Keywords

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