First highly enantioselective synthesis of benzodiazepinones by catalytic hydrogenation

Magnus Rueping; Estíbaliz Merino; René M. Koenigs

doi:10.1002/adsc.201000547

First highly enantioselective synthesis of benzodiazepinones by catalytic hydrogenation

Magnus Rueping^*, Estíbaliz Merino, René M. Koenigs

^*Corresponding author for this work

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

66 Scopus citations

Abstract

The first catalytic enantioselective synthesis of benzodiazepinones employing an efficient hydrogenation protocol has been developed. The corresponding products are obtained in good yields, with excellent enantioselectivities and broad functional group tolerance. In addition, a one-pot procedure involving in situ generation of benzodiazepin-2-ones followed by asymmetric reduction is presented.

Original language	English (US)
Pages (from-to)	2629-2634
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	352
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.201000547
State	Published - Oct 4 2010
Externally published	Yes

Keywords

Brønsted acids
Hantzsch dihydropyridines
asymmetric hydrogenation
enantioselective reduction
organocatalysis
β-amino acids

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201000547

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title = "First highly enantioselective synthesis of benzodiazepinones by catalytic hydrogenation",

abstract = "The first catalytic enantioselective synthesis of benzodiazepinones employing an efficient hydrogenation protocol has been developed. The corresponding products are obtained in good yields, with excellent enantioselectivities and broad functional group tolerance. In addition, a one-pot procedure involving in situ generation of benzodiazepin-2-ones followed by asymmetric reduction is presented.",

keywords = "Br{\o}nsted acids, Hantzsch dihydropyridines, asymmetric hydrogenation, enantioselective reduction, organocatalysis, β-amino acids",

author = "Magnus Rueping and Est{\'i}baliz Merino and Koenigs, {Ren{\'e} M.}",

year = "2010",

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language = "English (US)",

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journal = "Advanced Synthesis and Catalysis",

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T1 - First highly enantioselective synthesis of benzodiazepinones by catalytic hydrogenation

AU - Rueping, Magnus

AU - Merino, Estíbaliz

AU - Koenigs, René M.

PY - 2010/10/4

Y1 - 2010/10/4

N2 - The first catalytic enantioselective synthesis of benzodiazepinones employing an efficient hydrogenation protocol has been developed. The corresponding products are obtained in good yields, with excellent enantioselectivities and broad functional group tolerance. In addition, a one-pot procedure involving in situ generation of benzodiazepin-2-ones followed by asymmetric reduction is presented.

AB - The first catalytic enantioselective synthesis of benzodiazepinones employing an efficient hydrogenation protocol has been developed. The corresponding products are obtained in good yields, with excellent enantioselectivities and broad functional group tolerance. In addition, a one-pot procedure involving in situ generation of benzodiazepin-2-ones followed by asymmetric reduction is presented.

KW - Brønsted acids

KW - Hantzsch dihydropyridines

KW - asymmetric hydrogenation

KW - enantioselective reduction

KW - organocatalysis

KW - β-amino acids

UR - http://www.scopus.com/inward/record.url?scp=78449251697&partnerID=8YFLogxK

U2 - 10.1002/adsc.201000547

DO - 10.1002/adsc.201000547

M3 - Article

AN - SCOPUS:78449251697

SN - 1615-4150

VL - 352

SP - 2629

EP - 2634

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 14-15

ER -

First highly enantioselective synthesis of benzodiazepinones by catalytic hydrogenation

Abstract

Keywords

ASJC Scopus subject areas

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