Journal article
Tricarbonyls: Reactive Model Dienophiles for Asymmetric Diels-Alder Reactions
Synthesis (Stuttgart), Vol.1996(1), pp.105-110
1996
DOI: 10.1055/s-1996-4154
Abstract
he 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.
Details
- Title: Subtitle
- Tricarbonyls: Reactive Model Dienophiles for Asymmetric Diels-Alder Reactions
- Creators
- Hans-Joachim Lehmler - University of Iowa, Occupational and Environmental HealthMartin NiegerEberhard Breitmaier
- Resource Type
- Journal article
- Publication Details
- Synthesis (Stuttgart), Vol.1996(1), pp.105-110
- DOI
- 10.1055/s-1996-4154
- ISSN
- 0039-7881
- eISSN
- 1437-210X
- Language
- English
- Date published
- 1996
- Academic Unit
- Occupational and Environmental Health; Iowa Neuroscience Institute
- Record Identifier
- 9984001791602771
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