Enantioselective Brønsted acid catalyzed transfer hydrogenation: Organocatalytic reduction of imines

Magnus Rueping; Erli Sugiono; Cengiz Azap; Thomas Theissmann; Michael Bolte

doi:10.1021/ol0515964

Enantioselective Brønsted acid catalyzed transfer hydrogenation: Organocatalytic reduction of imines

Magnus Rueping^*, Erli Sugiono, Cengiz Azap, Thomas Theissmann, Michael Bolte

^*Corresponding author for this work

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

459 Scopus citations

Abstract

(Chemical Equation Presented) The first enantioselective Brønsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst.

Original language	English (US)
Pages (from-to)	3781-3783
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	17
DOIs	https://doi.org/10.1021/ol0515964
State	Published - Aug 18 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0515964

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title = "Enantioselective Br{\o}nsted acid catalyzed transfer hydrogenation: Organocatalytic reduction of imines",

abstract = "(Chemical Equation Presented) The first enantioselective Br{\o}nsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst.",

author = "Magnus Rueping and Erli Sugiono and Cengiz Azap and Thomas Theissmann and Michael Bolte",

year = "2005",

month = aug,

day = "18",

doi = "10.1021/ol0515964",

language = "English (US)",

volume = "7",

pages = "3781--3783",

journal = "Organic Letters",

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publisher = "American Chemical Society",

number = "17",

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TY - JOUR

T1 - Enantioselective Brønsted acid catalyzed transfer hydrogenation

T2 - Organocatalytic reduction of imines

AU - Rueping, Magnus

AU - Sugiono, Erli

AU - Azap, Cengiz

AU - Theissmann, Thomas

AU - Bolte, Michael

PY - 2005/8/18

Y1 - 2005/8/18

N2 - (Chemical Equation Presented) The first enantioselective Brønsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst.

AB - (Chemical Equation Presented) The first enantioselective Brønsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst.

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U2 - 10.1021/ol0515964

DO - 10.1021/ol0515964

M3 - Article

C2 - 16092874

AN - SCOPUS:24044465512

SN - 1523-7060

VL - 7

SP - 3781

EP - 3783

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Enantioselective Brønsted acid catalyzed transfer hydrogenation: Organocatalytic reduction of imines

Abstract

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