N-heterocycle construction via cyclic sulfamidates. Applications in synthesis.
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.
Bower
John F
JF
School of Chemistry, University of Bristol, Bristol, UK BS8 1TS.
Rujirawanich
Janjira
J
Gallagher
Timothy
T
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis; D003500:Cyclization; D007769:Lactams / Q000138:chemical synthesis*; D064704:Levofloxacin; D015242:Ofloxacin / Q000138:chemical synthesis; D017374:Paroxetine / Q000138:chemical synthesis; D011758:Pyrroles / Q000138:chemical synthesis; D013449:Sulfonamides / Q000138:chemical synthesis
D000900:Anti-Bacterial Agents; D001952:Bridged-Ring Compounds; D007769:Lactams; D011758:Pyrroles; D013449:Sulfonamides; C434304:aphanorphine; D017374:Paroxetine; D064704:Levofloxacin; D015242:Ofloxacin