Enantioselective organocatalytic reactions of 4-hydroxy-coumarin and 4-hydroxypyrone with α,β-unsaturated aldehydes - An efficient Michael addition-acetalization cascade to chromenones, quinolinones and pyranones

Magnus Rueping; Estíbaliz Merino; Erli Sugiono

doi:10.1002/adsc.200800340

Enantioselective organocatalytic reactions of 4-hydroxy-coumarin and 4-hydroxypyrone with α,β-unsaturated aldehydes - An efficient Michael addition-acetalization cascade to chromenones, quinolinones and pyranones

Magnus Rueping^*, Estíbaliz Merino, Erli Sugiono

^*Corresponding author for this work

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

89 Scopus citations

Abstract

An efficient, organocatalytic enantioselective addition-cyclization reaction of cyclic 1,3-dicarbonyl compounds with different α,β- unsaturated aldehydes has been developed. The diarylprolinol ether-catalyzed reaction cascade provides a variety of chromenones, quinolinones and pyranones in good yields and with excellent enantioselectivities.

Original language	English (US)
Pages (from-to)	2127-2131
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	350
Issue number	13
DOIs	https://doi.org/10.1002/adsc.200800340
State	Published - Sep 5 2008
Externally published	Yes

Keywords

Brønsted acids
Diarylprolinol ethers
Domino reaction
Iminium catalysis
Pyranocoumarins

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Enantioselective organocatalytic reactions of 4-hydroxy-coumarin and 4-hydroxypyrone with α,β-unsaturated aldehydes - An efficient Michael addition-acetalization cascade to chromenones, quinolinones and pyranones",

abstract = "An efficient, organocatalytic enantioselective addition-cyclization reaction of cyclic 1,3-dicarbonyl compounds with different α,β- unsaturated aldehydes has been developed. The diarylprolinol ether-catalyzed reaction cascade provides a variety of chromenones, quinolinones and pyranones in good yields and with excellent enantioselectivities.",

keywords = "Br{\o}nsted acids, Diarylprolinol ethers, Domino reaction, Iminium catalysis, Pyranocoumarins",

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

year = "2008",

month = sep,

day = "5",

doi = "10.1002/adsc.200800340",

language = "English (US)",

volume = "350",

pages = "2127--2131",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley",

number = "13",

}

Enantioselective organocatalytic reactions of 4-hydroxy-coumarin and 4-hydroxypyrone with α,β-unsaturated aldehydes - An efficient Michael addition-acetalization cascade to chromenones, quinolinones and pyranones. / Rueping, Magnus; Merino, Estíbaliz; Sugiono, Erli.
In: Advanced Synthesis and Catalysis, Vol. 350, No. 13, 05.09.2008, p. 2127-2131.

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

TY - JOUR

T1 - Enantioselective organocatalytic reactions of 4-hydroxy-coumarin and 4-hydroxypyrone with α,β-unsaturated aldehydes - An efficient Michael addition-acetalization cascade to chromenones, quinolinones and pyranones

AU - Rueping, Magnus

AU - Merino, Estíbaliz

AU - Sugiono, Erli

PY - 2008/9/5

Y1 - 2008/9/5

N2 - An efficient, organocatalytic enantioselective addition-cyclization reaction of cyclic 1,3-dicarbonyl compounds with different α,β- unsaturated aldehydes has been developed. The diarylprolinol ether-catalyzed reaction cascade provides a variety of chromenones, quinolinones and pyranones in good yields and with excellent enantioselectivities.

AB - An efficient, organocatalytic enantioselective addition-cyclization reaction of cyclic 1,3-dicarbonyl compounds with different α,β- unsaturated aldehydes has been developed. The diarylprolinol ether-catalyzed reaction cascade provides a variety of chromenones, quinolinones and pyranones in good yields and with excellent enantioselectivities.

KW - Brønsted acids

KW - Diarylprolinol ethers

KW - Domino reaction

KW - Iminium catalysis

KW - Pyranocoumarins

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U2 - 10.1002/adsc.200800340

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ER -

Enantioselective organocatalytic reactions of 4-hydroxy-coumarin and 4-hydroxypyrone with α,β-unsaturated aldehydes - An efficient Michael addition-acetalization cascade to chromenones, quinolinones and pyranones

Abstract

Keywords

ASJC Scopus subject areas

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