Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis

Chen Liu; Qiang Zhu; Kuo-Wei Huang; Yixin Lu

doi:10.1021/ol200747x

Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis

Chen Liu, Qiang Zhu, Kuo-Wei Huang, Yixin Lu

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

80 Scopus citations

Abstract

A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. © 2011 American Chemical Society.

Original language	English (US)
Pages (from-to)	2638-2641
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	10
DOIs	https://doi.org/10.1021/ol200747x
State	Published - May 20 2011

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1021/ol200747x

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title = "Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis",

abstract = "A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. {\textcopyright} 2011 American Chemical Society.",

author = "Chen Liu and Qiang Zhu and Kuo-Wei Huang and Yixin Lu",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112).",

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T1 - Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis

AU - Liu, Chen

AU - Zhu, Qiang

AU - Huang, Kuo-Wei

AU - Lu, Yixin

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112).

PY - 2011/5/20

Y1 - 2011/5/20

N2 - A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. © 2011 American Chemical Society.

AB - A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. © 2011 American Chemical Society.

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EP - 2641

JO - Organic Letters

JF - Organic Letters

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ER -

Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis

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