Silica gel catalyzed cyclizations of enones and double michael additions of vinylogous amides: Efficient synthesis of bicyclo[2.2.2]octanones and bicyclo-hydrocarbazolones

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OriginalspracheEnglisch
Seiten (von - bis)34-35
Seitenumfang2
FachzeitschriftSYNLETT
Jahrgang1989
Ausgabenummer1
PublikationsstatusVeröffentlicht - Sept. 1989

Abstract

Mixed ketene acetals of enones of type 2 undergo stereoselective cydizations on a short column of silica gel to yield bicyclo[2.22]octanones of type 3. Enolates of vinylogous amides of types 6 and 8 cyclize directly upon reaction with methyl acrylate at -78 °C to form bicyclic β-amino ketones of types 7 and 9.

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Silica gel catalyzed cyclizations of enones and double michael additions of vinylogous amides: Efficient synthesis of bicyclo[2.2.2]octanones and bicyclo-hydrocarbazolones. / Schinzer, Dieter; Kalesse, Markus.
in: SYNLETT, Jahrgang 1989, Nr. 1, 09.1989, S. 34-35.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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abstract = "Mixed ketene acetals of enones of type 2 undergo stereoselective cydizations on a short column of silica gel to yield bicyclo[2.22]octanones of type 3. Enolates of vinylogous amides of types 6 and 8 cyclize directly upon reaction with methyl acrylate at -78 °C to form bicyclic β-amino ketones of types 7 and 9.",
author = "Dieter Schinzer and Markus Kalesse",
note = "Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft (DFG) and the Fonds der Chemischen Industrie.",
year = "1989",
month = sep,
doi = "10.1055/s-1989-34704",
language = "English",
volume = "1989",
pages = "34--35",
journal = "SYNLETT",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
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T1 - Silica gel catalyzed cyclizations of enones and double michael additions of vinylogous amides

T2 - Efficient synthesis of bicyclo[2.2.2]octanones and bicyclo-hydrocarbazolones

AU - Schinzer, Dieter

AU - Kalesse, Markus

N1 - Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft (DFG) and the Fonds der Chemischen Industrie.

PY - 1989/9

Y1 - 1989/9

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AB - Mixed ketene acetals of enones of type 2 undergo stereoselective cydizations on a short column of silica gel to yield bicyclo[2.22]octanones of type 3. Enolates of vinylogous amides of types 6 and 8 cyclize directly upon reaction with methyl acrylate at -78 °C to form bicyclic β-amino ketones of types 7 and 9.

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DO - 10.1055/s-1989-34704

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VL - 1989

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EP - 35

JO - SYNLETT

JF - SYNLETT

SN - 0936-5214

IS - 1

ER -

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