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Synthesis 1991; 1991(12): 1130-1136
DOI: 10.1055/s-1991-28404
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Highly SN2′-, (E)-, and Antiselective Alkylation of Allylic Phosphates. Facile Synthesis of Coenzyme Q10

Akira Yanagisawa* , Nobuyoshi Nomura, Yoshiyuki Noritake, Hisashi Yamamoto
  • *Department of Applied Chemistry, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
29 April 2002 (online)

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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.