Highly SN2′-, (E)-, and Antiselective Alkylation of Allylic Phosphates. Facile Synthesis of Coenzyme Q10
- 1 January 1991
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1991 (12) , 1130-1136
- https://doi.org/10.1055/s-1991-28404
Abstract
Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent in the presence of CuCN · 2 LiCl gave geraniol or farnesol derivatives with high SN2′ selectivity. Phosphate leaving groups were highly trans-stereoselective for the formation of (E,E)-farnesol derivatives. Furthermore, complete anti-SN2′ selectivity was observed in the alkylation of optically active allylic phosphates. The present method appears to be an excellent carbon-carbon coupling reaction with high regio-, (E)-, and enantioselectivity. Coenzyme Q10 (ubiquinone 10) was efficiently synthesized using this methodology.Keywords
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