Ring-closing metathesis of α-ester-substituted enol ethers: application to the shortest synthesis of KDO
2003; Elsevier BV; Volume: 59; Issue: 35 Linguagem: Inglês
10.1016/s0040-4020(03)00819-6
ISSN1464-5416
AutoresKoen F. W. Hekking, Floris L. van Delft, Floris P. J. T. Rutjes,
Tópico(s)Chemical Synthesis and Analysis
ResumoRing-closing metathesis reactions of α-ester-substituted enol ethers are described. In the case of unsubstituted terminal olefins, isomerization prior to cyclization was observed as an undesired side reaction, which could not be completely inhibited. Furthermore, this methodology was applied to a formal synthesis of KDO, which now represents the shortest synthetic pathway to KDO and its deoxy analogue. Interestingly, in this route olefin isomerization was not observed, presumably due to the increased steric environment of the double bond. Finally, an efficient two-step conversion to transform an alcohol into an α-alkoxy acrylate is also described.
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