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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Tether-controlled cycloadditions for the asymmetric synthesis of decalins: increased selectivity in acetonitrile solvent.

[reaction: see text] The beneficial influence of cis-isopropylidene acetal tether control groups, to facilitate the asymmetric synthesis of substituted decalins by intramolecular Diels-Alder reactions, is described. Compared to trans-acetonides, these cases proceed under milder conditions to afford the cis-fused adducts from an endo transition state. An unusual acetonitrile solvent effect exerts a dramatic influence on the diastereoselectivity. This strategy leads to the chiral nonracemic bicyclo[4.4.0]decane core of diverse natural products.[1]

References

  1. Tether-controlled cycloadditions for the asymmetric synthesis of decalins: increased selectivity in acetonitrile solvent. Melekhov, A., Forgione, P., Legoupy, S., Fallis, A.G. Org. Lett. (2000) [Pubmed]
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