Superiority of Phosphate Ester as Leaving Group for Organocopper Reactions. Highly SN2′ -, (E)-, and Antiselective Alkylation of Allylic Alcohol Derivatives
- 1 January 1991
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1991 (04) , 251-253
- https://doi.org/10.1055/s-1991-20696
Abstract
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.Keywords
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