Synthesis of functionalized cyclopentanes, cyclohexanes and cycloheptanes by a silicon-induced domino reaction

verfasst von

Tycho Michel, Andreas Kirschning, Christian Beier, Nico Bräuer, Ernst Schaumann, Gunadi Adiwidjaja

Abstract

1,3-Functionalized cyclopentanes, -hexanes and -heptanes are obtained by addition of lithiated silyldithioacetals 7 to epoxyhomoallyl tosylates 4-6. The reaction involves a cascade of epoxide ring opening, of Brook 1,4-rearrangement and tosylate substitution. The method is particularly suitable for the preparation of cyclopentanes, whereas cyclohexanes and -heptanes are formed in yields only up to 49%. Use of enantiomerically pure epoxides provides optically active cyclopentanes (S)-10b, d, 11a as well as oxetanes (S)-14a, b. Hydrolysis of the dithioacetal function leads to the corresponding ketones 12. Cyclization of epoxide 24b gives an anellated cyclopentane 26, the configuration of which was established by X-ray structural analysis of dinitrobenzoate 27. Use of epoxide 29b provides the anellated tetrahydrofuran 30.

Externe Organisation(en)

Technische Universität Clausthal
Universität Hamburg

Typ

Artikel

Journal

Liebigs Annales

Seiten

1811-1821

Anzahl der Seiten

11

ISSN

0947-3440

Publikationsdatum

22.10.1996

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Allgemeine Chemie

Elektronische Version(en)

https://doi.org/10.1002/jlac.199619961115 (Zugang: Unbekannt)