A highly enantioselective Brønsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids

Magnus Rueping; Andrey P. Antonchick; Thomas Theissmann

doi:10.1002/anie.200600191

A highly enantioselective Brønsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids

Magnus Rueping^*, Andrey P. Antonchick, Thomas Theissmann

^*Corresponding author for this work

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

653 Scopus citations

Abstract

(Chemical Equation Presented) A categorical success: A Brønsted acid catalyzed cascade transfer hydrogenation provides direct access to 2-aryl- and 2-alkyl-substituted tetrahydroquinolines with excellent enantioselectivities under mild conditions and using very low amounts of catalyst (see scheme). The best results were achieved with the binol phosphate catalyst, where Ar = 9-phenanthryl, used successfully in the Strecker reaction.

Original language	English (US)
Pages (from-to)	3683-3686
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	22
DOIs	https://doi.org/10.1002/anie.200600191
State	Published - May 26 2006
Externally published	Yes

Keywords

Asymmetric hydrogenation
Brønsted acid
Hantzsch dihydropyridine
Organocatalysis
Tetrahydroquinoline

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200600191

Cite this

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title = "A highly enantioselective Br{\o}nsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids",

abstract = "(Chemical Equation Presented) A categorical success: A Br{\o}nsted acid catalyzed cascade transfer hydrogenation provides direct access to 2-aryl- and 2-alkyl-substituted tetrahydroquinolines with excellent enantioselectivities under mild conditions and using very low amounts of catalyst (see scheme). The best results were achieved with the binol phosphate catalyst, where Ar = 9-phenanthryl, used successfully in the Strecker reaction.",

keywords = "Asymmetric hydrogenation, Br{\o}nsted acid, Hantzsch dihydropyridine, Organocatalysis, Tetrahydroquinoline",

author = "Magnus Rueping and Antonchick, {Andrey P.} and Thomas Theissmann",

year = "2006",

month = may,

day = "26",

doi = "10.1002/anie.200600191",

language = "English (US)",

volume = "45",

pages = "3683--3686",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley",

number = "22",

}

A highly enantioselective Brønsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids. / Rueping, Magnus; Antonchick, Andrey P.; Theissmann, Thomas.
In: Angewandte Chemie - International Edition, Vol. 45, No. 22, 26.05.2006, p. 3683-3686.

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

TY - JOUR

T1 - A highly enantioselective Brønsted acid catalyzed cascade reaction

T2 - Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids

AU - Rueping, Magnus

AU - Antonchick, Andrey P.

AU - Theissmann, Thomas

PY - 2006/5/26

Y1 - 2006/5/26

N2 - (Chemical Equation Presented) A categorical success: A Brønsted acid catalyzed cascade transfer hydrogenation provides direct access to 2-aryl- and 2-alkyl-substituted tetrahydroquinolines with excellent enantioselectivities under mild conditions and using very low amounts of catalyst (see scheme). The best results were achieved with the binol phosphate catalyst, where Ar = 9-phenanthryl, used successfully in the Strecker reaction.

AB - (Chemical Equation Presented) A categorical success: A Brønsted acid catalyzed cascade transfer hydrogenation provides direct access to 2-aryl- and 2-alkyl-substituted tetrahydroquinolines with excellent enantioselectivities under mild conditions and using very low amounts of catalyst (see scheme). The best results were achieved with the binol phosphate catalyst, where Ar = 9-phenanthryl, used successfully in the Strecker reaction.

KW - Asymmetric hydrogenation

KW - Brønsted acid

KW - Hantzsch dihydropyridine

KW - Organocatalysis

KW - Tetrahydroquinoline

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U2 - 10.1002/anie.200600191

DO - 10.1002/anie.200600191

M3 - Article

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VL - 45

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 22

ER -

A highly enantioselective Brønsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids

Abstract

Keywords

ASJC Scopus subject areas

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