Stereoselective Inter- and Intramolecular Pauson–Khand Reactions of N-(2-Alkynoyl) Derivatives of Chiral Oxazolidin-2-ones
✍ Scribed by Sílvia Fonquerna; Ramon Rios; Albert Moyano; Miquel A. Pericàs; Antoni Riera
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 697 KB
- Volume
- 1999
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
A complete account of the intermolecular and intramolecular moieties, can be very high (up to 17.5:1 dr) for the formation of 1,4-dicarbonyl regioisomers, and the diastereomeric Pauson-Khand reactions of N-(2-alkynoyl) derivatives of chiral 2-oxazolidinones is presented. The intermolecular products can often be separated by column chromatography.
Under the appropriate conditions, the intramolecular Pauson-Khand reactions with norbornene or norbornadiene take place under mild conditions and in high yields. Phenyl-Pauson-Khand reactions of oxazolidinone-derived enynes can also take place with very good yields, but with low or trimethylsilylpropiolate derivatives lead to the exclusive formation of 1,4-dicarbonyl regioisomers, while mixtures of diastereoselectivities. The absolute configurations of several adducts have been determined, and the stereochemical 1,3-and 1,4-regioisomers are obtained with tetrolate derivatives. The diastereoselectivity of the reaction, outcome of the reaction has been rationalized. determined by the substitution pattern of the oxazolidinone use of chiral alcohols or thiols as temporary stereochemical
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