Asymmetric Brønsted acid catalysis: Catalytic enantioselective synthesis of highly biologically active dihydroquinazolinones

Magnus Rueping; Andrey P. Antonchick; Erli Sugiono; Konstantin Grenader

doi:10.1002/anie.200804770

Asymmetric Brønsted acid catalysis: Catalytic enantioselective synthesis of highly biologically active dihydroquinazolinones

Magnus Rueping^*, Andrey P. Antonchick, Erli Sugiono, Konstantin Grenader

^*Corresponding author for this work

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

202 Scopus citations

Abstract

(Chemical Equation Presented) Surprisingly straightforward: A metal-free, highly enantioselective Brønsted acid catalyzed condensation/addition reaction has been developed for the construction of 2,3-dihydroquinazolinones starting from 2-aminobenzamide and aldehydes (see scheme). This efficient approach provides 2,3-dihydroquinazolinones with a strong preference for the S enantiomers, which have higher biological activities than the R enantiomers.

Original language	English (US)
Pages (from-to)	908-910
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	5
DOIs	https://doi.org/10.1002/anie.200804770
State	Published - Jan 19 2009
Externally published	Yes

Keywords

Antitumor agents
Inhibitors
Organocatalysis
Phosphoric acid diester

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.200804770

Cite this

@article{bbff036c561441b88d849b6ad250f37a,

title = "Asymmetric Br{\o}nsted acid catalysis: Catalytic enantioselective synthesis of highly biologically active dihydroquinazolinones",

abstract = "(Chemical Equation Presented) Surprisingly straightforward: A metal-free, highly enantioselective Br{\o}nsted acid catalyzed condensation/addition reaction has been developed for the construction of 2,3-dihydroquinazolinones starting from 2-aminobenzamide and aldehydes (see scheme). This efficient approach provides 2,3-dihydroquinazolinones with a strong preference for the S enantiomers, which have higher biological activities than the R enantiomers.",

keywords = "Antitumor agents, Inhibitors, Organocatalysis, Phosphoric acid diester",

author = "Magnus Rueping and Antonchick, {Andrey P.} and Erli Sugiono and Konstantin Grenader",

year = "2009",

month = jan,

day = "19",

doi = "10.1002/anie.200804770",

language = "English (US)",

volume = "48",

pages = "908--910",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley",

number = "5",

}

TY - JOUR

T1 - Asymmetric Brønsted acid catalysis

T2 - Catalytic enantioselective synthesis of highly biologically active dihydroquinazolinones

AU - Rueping, Magnus

AU - Antonchick, Andrey P.

AU - Sugiono, Erli

AU - Grenader, Konstantin

PY - 2009/1/19

Y1 - 2009/1/19

N2 - (Chemical Equation Presented) Surprisingly straightforward: A metal-free, highly enantioselective Brønsted acid catalyzed condensation/addition reaction has been developed for the construction of 2,3-dihydroquinazolinones starting from 2-aminobenzamide and aldehydes (see scheme). This efficient approach provides 2,3-dihydroquinazolinones with a strong preference for the S enantiomers, which have higher biological activities than the R enantiomers.

AB - (Chemical Equation Presented) Surprisingly straightforward: A metal-free, highly enantioselective Brønsted acid catalyzed condensation/addition reaction has been developed for the construction of 2,3-dihydroquinazolinones starting from 2-aminobenzamide and aldehydes (see scheme). This efficient approach provides 2,3-dihydroquinazolinones with a strong preference for the S enantiomers, which have higher biological activities than the R enantiomers.

KW - Antitumor agents

KW - Inhibitors

KW - Organocatalysis

KW - Phosphoric acid diester

UR - http://www.scopus.com/inward/record.url?scp=58349118504&partnerID=8YFLogxK

U2 - 10.1002/anie.200804770

DO - 10.1002/anie.200804770

M3 - Article

C2 - 19101974

AN - SCOPUS:58349118504

SN - 1433-7851

VL - 48

SP - 908

EP - 910

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

Asymmetric Brønsted acid catalysis: Catalytic enantioselective synthesis of highly biologically active dihydroquinazolinones

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this