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Issue 22, 1997
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1,5-Asymmetric induction of chirality: highly diastereoselective synthesis of homoallylic tertiary alcohols by the Lewis acid-mediated addition of allylstannanes into ketones in the side-chain of π-allyltricarbonyliron lactone complexes

Steven V. Ley  and  Liam R. Cox 

Abstract

Allylstannanes add into ketone groups in the side-chain of π-allyltricarbonyliron lactone complexes to afford the corresponding homoallylic tertiary alcohol complexes with very high levels of diastereocontrol. The reaction provides an example of 1,5-asymmetric induction of chirality with the lactone tether acting as the source of induction. The endo addition complexes can be converted into (E,E )-dienes bearing an α tertiary alcohol chiral centre in two steps proceeding via the η4-dienetricarbonyliron complexes. No loss of enantio- or diastereo-purity is observed during decomplexation.

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Article type: Paper
DOI: 10.1039/A704491G
Citation: J. Chem. Soc., Perkin Trans. 1, 1997,0, 3315-3326
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    1,5-Asymmetric induction of chirality: highly diastereoselective synthesis of homoallylic tertiary alcohols by the Lewis acid-mediated addition of allylstannanes into ketones in the side-chain of π-allyltricarbonyliron lactone complexes

    S. V. Ley and L. R. Cox, J. Chem. Soc., Perkin Trans. 1, 1997, 0, 3315
    DOI: 10.1039/A704491G

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