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Issue 7, 2010
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N-Heterocycle construction via cyclic sulfamidates. Applications in synthesis

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Abstract

When combined with an appropriate nucleophilic component, 1,2- and 1,3-cyclic sulfamidates function as versatile precursors to a range of substituted and enantiopure heterocyclic classes. Functionalised enolates provide a direct entry to C-3 functionalised lactams, as exemplified by total syntheses of (−)-aphanorphine, (+)-laccarin and (−)-paroxetine. Heteroatom nucleophiles, such as thiol esters, amino esters and bromo phenols, provide concise access to a range of enantiomerically pure thiomorpholine, piperazine and benzofused heterocyclic scaffolds. The latter methodology enables a facile synthesis of the antibacteriocidal agent levofloxacin.

Graphical abstract: N-Heterocycle construction via cyclic sulfamidates. Applications in synthesis

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Publication details

The article was received on 19 Oct 2009, accepted on 21 Dec 2009 and first published on 28 Jan 2010


Article type: Perspective
DOI: 10.1039/B921842D
Citation: Org. Biomol. Chem., 2010,8, 1505-1519

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    N-Heterocycle construction via cyclic sulfamidates. Applications in synthesis

    J. F. Bower, J. Rujirawanich and T. Gallagher, Org. Biomol. Chem., 2010, 8, 1505
    DOI: 10.1039/B921842D

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