Tricarbonyls: Reactive Model Dienophiles for Asymmetric Diels-Alder Reactions

Hans-Joachim Lehmler; Martin Nieger; Eberhard Breitmaier

doi:10.1055/s-1996-4154

Synthesis 1996; 1996(1): 105-110
DOI: 10.1055/s-1996-4154

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Tricarbonyls: Reactive Model Dienophiles for Asymmetric Diels-Alder Reactions

Hans-Joachim Lehmler¹ , Martin Nieger² , Eberhard Breitmaier¹

¹Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany, Fax +49(228)735683
²Institut für Anorganische Chemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

The hetero-Diels-Alder reaction of 2-methyl-1-(1-phenylalkoxy)-butadienes 5a-d with cyclic triketones proceeds smoothly at room temperature in excellent yield and high diastereoselectivity. The configuration of the cycloadducts 6a and 6b was determined by X-ray single crystal analysis. Mild acidic hydrolysis of the cycloadduct 6a using SiO₂ as a promoter yielded an α,β-unsaturated aldehyde trans-9. The trans-epoxides 10a-d can be obtained from 6a-d using a freshly prepared solution of dimethyldioxirane in acetone.

hetero-Diels-Alder reaction - 2-methyl-1-(1-phenylalkoxy)-1,3-butadienes - indanetrione - alloxane - dimethyldioxirane

PDF (468 kb)