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Issue 7, 2006
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Ligand-mediated enantioselective addition of lithium carbazolates to aldehydes

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Abstract

The enantioselective synthesis of acyclic pyrrole, indole and other N-carbazole carbinols via ligand-mediated addition of lithium carbazolates to aldehydes, together with studies into their catalytic enantioselective synthesis using substoichiometric base and ligand, are reported. The subsequent exploitation of the resulting stereocentre as a controlling element in 1,3-syn- and anti-selective reduction of β-ketones and elaboration to homoallylic alcohols is also described.

Graphical abstract: Ligand-mediated enantioselective addition of lithium carbazolates to aldehydes

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Publication details

The article was received on 28 Oct 2005, accepted on 13 Dec 2005 and first published on 27 Feb 2006


Article type: Paper
DOI: 10.1039/B515356E
Citation: Org. Biomol. Chem., 2006,4, 1313-1327
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    Ligand-mediated enantioselective addition of lithium carbazolates to aldehydes

    M. S. Scott, A. C. Lucas, C. A. Luckhurst, J. C. Prodger and D. J. Dixon, Org. Biomol. Chem., 2006, 4, 1313
    DOI: 10.1039/B515356E

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