Asymmetric counterion pair catalysis: An enantioselective Brønsted acid-catalyzed protonation

Magnus Rueping; Thomas Theissmann; Sadiya Raja; Jan W. Bats

doi:10.1002/adsc.200800020

Asymmetric counterion pair catalysis: An enantioselective Brønsted acid-catalyzed protonation

Magnus Rueping^*, Thomas Theissmann, Sadiya Raja, Jan W. Bats

^*Corresponding author for this work

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

167 Scopus citations

Abstract

A new asymmetric Brønsted acid-catalyzed cascade reaction involving a 1,4-addition, enantioselective protonation and 1,2-addition has been developed. This organocatalytic cascade not only provides for the first time 3-and 2,3-substituted tetrahydroquinolines and octahydroacridines in good yields with high dia- and enantioselectivities under mild reaction conditions but additionally represents the first example of a chiral Brønsted acid-catalyzed protonation reaction in an organocatalytic domino reaction. Furthermore, the new Brønsted acid-catalyzed hydride-proton-hydride transfer cascade can be applied to prepare new molecular scaffolds with up to three new stereocenters in an efficient one-pot reaction sequence.

Original language	English (US)
Pages (from-to)	1001-1006
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	350
Issue number	7-8
DOIs	https://doi.org/10.1002/adsc.200800020
State	Published - May 5 2008
Externally published	Yes

Keywords

BINOL phosphate
Enantioselective isomerization
Hantzsch dihydropyridine
Organocatalytic cascade reaction
Transfer hydrogenation

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200800020

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title = "Asymmetric counterion pair catalysis: An enantioselective Br{\o}nsted acid-catalyzed protonation",

abstract = "A new asymmetric Br{\o}nsted acid-catalyzed cascade reaction involving a 1,4-addition, enantioselective protonation and 1,2-addition has been developed. This organocatalytic cascade not only provides for the first time 3-and 2,3-substituted tetrahydroquinolines and octahydroacridines in good yields with high dia- and enantioselectivities under mild reaction conditions but additionally represents the first example of a chiral Br{\o}nsted acid-catalyzed protonation reaction in an organocatalytic domino reaction. Furthermore, the new Br{\o}nsted acid-catalyzed hydride-proton-hydride transfer cascade can be applied to prepare new molecular scaffolds with up to three new stereocenters in an efficient one-pot reaction sequence.",

keywords = "BINOL phosphate, Enantioselective isomerization, Hantzsch dihydropyridine, Organocatalytic cascade reaction, Transfer hydrogenation",

author = "Magnus Rueping and Thomas Theissmann and Sadiya Raja and Bats, {Jan W.}",

year = "2008",

month = may,

day = "5",

doi = "10.1002/adsc.200800020",

language = "English (US)",

volume = "350",

pages = "1001--1006",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley",

number = "7-8",

}

TY - JOUR

T1 - Asymmetric counterion pair catalysis

T2 - An enantioselective Brønsted acid-catalyzed protonation

AU - Rueping, Magnus

AU - Theissmann, Thomas

AU - Raja, Sadiya

AU - Bats, Jan W.

PY - 2008/5/5

Y1 - 2008/5/5

N2 - A new asymmetric Brønsted acid-catalyzed cascade reaction involving a 1,4-addition, enantioselective protonation and 1,2-addition has been developed. This organocatalytic cascade not only provides for the first time 3-and 2,3-substituted tetrahydroquinolines and octahydroacridines in good yields with high dia- and enantioselectivities under mild reaction conditions but additionally represents the first example of a chiral Brønsted acid-catalyzed protonation reaction in an organocatalytic domino reaction. Furthermore, the new Brønsted acid-catalyzed hydride-proton-hydride transfer cascade can be applied to prepare new molecular scaffolds with up to three new stereocenters in an efficient one-pot reaction sequence.

AB - A new asymmetric Brønsted acid-catalyzed cascade reaction involving a 1,4-addition, enantioselective protonation and 1,2-addition has been developed. This organocatalytic cascade not only provides for the first time 3-and 2,3-substituted tetrahydroquinolines and octahydroacridines in good yields with high dia- and enantioselectivities under mild reaction conditions but additionally represents the first example of a chiral Brønsted acid-catalyzed protonation reaction in an organocatalytic domino reaction. Furthermore, the new Brønsted acid-catalyzed hydride-proton-hydride transfer cascade can be applied to prepare new molecular scaffolds with up to three new stereocenters in an efficient one-pot reaction sequence.

KW - BINOL phosphate

KW - Enantioselective isomerization

KW - Hantzsch dihydropyridine

KW - Organocatalytic cascade reaction

KW - Transfer hydrogenation

UR - http://www.scopus.com/inward/record.url?scp=53249093355&partnerID=8YFLogxK

U2 - 10.1002/adsc.200800020

DO - 10.1002/adsc.200800020

M3 - Article

AN - SCOPUS:53249093355

SN - 1615-4150

VL - 350

SP - 1001

EP - 1006

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 7-8

ER -

Asymmetric counterion pair catalysis: An enantioselective Brønsted acid-catalyzed protonation

Abstract

Keywords

ASJC Scopus subject areas

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