Asymmetric iminium ion catalysis: An efficient enantioselective synthesis of pyranonaphthoquinones and β-lapachones

Magnus Rueping; Erli Sugiono; Estíbaliz Merino

doi:10.1002/anie.200705110

Asymmetric iminium ion catalysis: An efficient enantioselective synthesis of pyranonaphthoquinones and β-lapachones

Magnus Rueping^*, Erli Sugiono, Estíbaliz Merino

^*Corresponding author for this work

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

149 Scopus citations

Abstract

(Chemical Equation Presented) An addition-cyclization reaction cascade triggeredby an organocatalyst was used for the enantioselective preparation of a series of biologically active 1,2- and 1,4-pyranonaphthoquinones from aliphatic andaromatic α,β-unsaturated aldehydes and2-hydroxy-1-4- naphthoquinone. A trimethylsilyl-protected diarylprolinol serves as the Lewis base organocatalyst.

Original language	English (US)
Pages (from-to)	3046-3049
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	16
DOIs	https://doi.org/10.1002/anie.200705110
State	Published - Apr 7 2008
Externally published	Yes

Keywords

Iminium ions
Lapachones
Lewis base catalysis
Naphthoquinones
Organocatalysis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200705110

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abstract = "(Chemical Equation Presented) An addition-cyclization reaction cascade triggeredby an organocatalyst was used for the enantioselective preparation of a series of biologically active 1,2- and 1,4-pyranonaphthoquinones from aliphatic andaromatic α,β-unsaturated aldehydes and2-hydroxy-1-4- naphthoquinone. A trimethylsilyl-protected diarylprolinol serves as the Lewis base organocatalyst.",

keywords = "Iminium ions, Lapachones, Lewis base catalysis, Naphthoquinones, Organocatalysis",

author = "Magnus Rueping and Erli Sugiono and Est{\'i}baliz Merino",

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T2 - An efficient enantioselective synthesis of pyranonaphthoquinones and β-lapachones

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AU - Sugiono, Erli

AU - Merino, Estíbaliz

PY - 2008/4/7

Y1 - 2008/4/7

N2 - (Chemical Equation Presented) An addition-cyclization reaction cascade triggeredby an organocatalyst was used for the enantioselective preparation of a series of biologically active 1,2- and 1,4-pyranonaphthoquinones from aliphatic andaromatic α,β-unsaturated aldehydes and2-hydroxy-1-4- naphthoquinone. A trimethylsilyl-protected diarylprolinol serves as the Lewis base organocatalyst.

AB - (Chemical Equation Presented) An addition-cyclization reaction cascade triggeredby an organocatalyst was used for the enantioselective preparation of a series of biologically active 1,2- and 1,4-pyranonaphthoquinones from aliphatic andaromatic α,β-unsaturated aldehydes and2-hydroxy-1-4- naphthoquinone. A trimethylsilyl-protected diarylprolinol serves as the Lewis base organocatalyst.

KW - Iminium ions

KW - Lapachones

KW - Lewis base catalysis

KW - Naphthoquinones

KW - Organocatalysis

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 16

ER -

Asymmetric iminium ion catalysis: An efficient enantioselective synthesis of pyranonaphthoquinones and β-lapachones

Abstract

Keywords

ASJC Scopus subject areas

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