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Synlett 1991; 1991(4): 251-253
DOI: 10.1055/s-1991-20696
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Superiority of Phosphate Ester as Leaving Group for Organocopper Reactions. Highly SN2′ -, (E)-, and Antiselective Alkylation of Allylic Alcohol Derivatives

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

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Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent (3-methyl-2-butenylmagnesium chloride) in the presence of CuCN.2LiCl 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 regio-, (E)-, and enantioselectivity.