Issue 7, 2010

N-Heterocycle construction via cyclic sulfamidates. Applications in synthesis

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

Article information

Article type
Perspective
Submitted
19 Oct 2009
Accepted
21 Dec 2009
First published
28 Jan 2010

Org. Biomol. Chem., 2010,8, 1505-1519

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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