Asymmetric Hetero-Diels-Alder Reactions with Heterocumulenes. -Chiral 2-alkenyloxazolines or thiazolines (I) and (IV) undergo hetero-Diels-Alder reaction with the ketene (II) or the isocyanate (VI) giving adducts with complete stereocontrol. In the case of oxazoline (I) a fast second addition yield
Asymmetric hetero-Diels-Alder reactions. Mechanism of the reaction of alkenyloxazolines with isocyanates
β Scribed by Mark C. Elliott; Elbertus Kruiswijk; David J. Willock
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 309 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Diastereomerically pure oxazolo[3,
pyrimidines can be readily prepared by the reaction of alkenyloxazolines with isocyanates. These compounds undergo epimerisation upon prolonged heating. The mechanism of this transformation has been investigated experimentally and computationally.
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