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Issue 16, 1993
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Stereochemical control (E/Z and syn/anti) by the diphenylphosphinoyl group in the synthesis of allylic alcohols by allylic rearrangement and by 1,4-diastereoselective reduction of enones

Abstract

Allylic rearrangement of substitued 2-hydroxyalk-3-en-1-yl(diphenyl)phosphine oxides to 4-hydroxyalk-2-en-1-yl(diphenyl)phosphine oxides can be performed with total regio- and reasonable stereochemical control. Alternatively, the reduction of substituted 4-diphenylphosphinoylbut-2-en-1 -ones shows remarkable 1,4-diastereoselectivity. All these reactions are directed by the diphenylphosphinoyl (Ph2PO) group.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1993, 1849-1859
Article type
Paper

Stereochemical control (E/Z and syn/anti) by the diphenylphosphinoyl group in the synthesis of allylic alcohols by allylic rearrangement and by 1,4-diastereoselective reduction of enones

J. Clayden, E. W. Collington, J. Elliott, S. J. Martin, A. B. McElroy, S. Warren and D. Waterson, J. Chem. Soc., Perkin Trans. 1, 1993, 1849
DOI: 10.1039/P19930001849

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