Remarkably low catalyst loading in brønsted acid catalyzed transfer hydrogenations: Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones

Magnus Rueping; Andrey P. Antonchick; Thomas Theissmann

doi:10.1002/anie.200601832

Remarkably low catalyst loading in brønsted acid catalyzed transfer hydrogenations: Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones

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

^*Corresponding author for this work

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

285 Scopus citations

Abstract

(Chemical Equation Presented) A highly efficient transfer hydrogenation of benzoxazines, benzothiazines, and benzoxazinones with as low as 0.01 mol % binol phosphate catalyst furnishes the dihydro-2H-benzoxazines, -benzothiazines, and -benzoxazinones in good yields and with excellent enantioselectivities (see scheme). Particularly noteworthy are the mild reaction conditions and the wide scope of substrates, including sulfur-containing compounds.

Original language	English (US)
Pages (from-to)	6751-6755
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	40
DOIs	https://doi.org/10.1002/anie.200601832
State	Published - Oct 13 2006
Externally published	Yes

Keywords

Binol phosphate
Brønsted acids
Enantioselective hydrogenation
Hantzsch dihydropyridine
Ion-pair catalysis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200601832

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title = "Remarkably low catalyst loading in br{\o}nsted acid catalyzed transfer hydrogenations: Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones",

abstract = "(Chemical Equation Presented) A highly efficient transfer hydrogenation of benzoxazines, benzothiazines, and benzoxazinones with as low as 0.01 mol % binol phosphate catalyst furnishes the dihydro-2H-benzoxazines, -benzothiazines, and -benzoxazinones in good yields and with excellent enantioselectivities (see scheme). Particularly noteworthy are the mild reaction conditions and the wide scope of substrates, including sulfur-containing compounds.",

keywords = "Binol phosphate, Br{\o}nsted acids, Enantioselective hydrogenation, Hantzsch dihydropyridine, Ion-pair catalysis",

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

year = "2006",

month = oct,

day = "13",

doi = "10.1002/anie.200601832",

language = "English (US)",

volume = "45",

pages = "6751--6755",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley",

number = "40",

}

Remarkably low catalyst loading in brønsted acid catalyzed transfer hydrogenations: Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones. / Rueping, Magnus; Antonchick, Andrey P.; Theissmann, Thomas.
In: Angewandte Chemie - International Edition, Vol. 45, No. 40, 13.10.2006, p. 6751-6755.

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

TY - JOUR

T1 - Remarkably low catalyst loading in brønsted acid catalyzed transfer hydrogenations

T2 - Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones

AU - Rueping, Magnus

AU - Antonchick, Andrey P.

AU - Theissmann, Thomas

PY - 2006/10/13

Y1 - 2006/10/13

N2 - (Chemical Equation Presented) A highly efficient transfer hydrogenation of benzoxazines, benzothiazines, and benzoxazinones with as low as 0.01 mol % binol phosphate catalyst furnishes the dihydro-2H-benzoxazines, -benzothiazines, and -benzoxazinones in good yields and with excellent enantioselectivities (see scheme). Particularly noteworthy are the mild reaction conditions and the wide scope of substrates, including sulfur-containing compounds.

AB - (Chemical Equation Presented) A highly efficient transfer hydrogenation of benzoxazines, benzothiazines, and benzoxazinones with as low as 0.01 mol % binol phosphate catalyst furnishes the dihydro-2H-benzoxazines, -benzothiazines, and -benzoxazinones in good yields and with excellent enantioselectivities (see scheme). Particularly noteworthy are the mild reaction conditions and the wide scope of substrates, including sulfur-containing compounds.

KW - Binol phosphate

KW - Brønsted acids

KW - Enantioselective hydrogenation

KW - Hantzsch dihydropyridine

KW - Ion-pair catalysis

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U2 - 10.1002/anie.200601832

DO - 10.1002/anie.200601832

M3 - Article

C2 - 16986184

AN - SCOPUS:33750148995

SN - 1433-7851

VL - 45

SP - 6751

EP - 6755

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 40

ER -

Remarkably low catalyst loading in brønsted acid catalyzed transfer hydrogenations: Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones

Abstract

Keywords

ASJC Scopus subject areas

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