Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 Apr 7;8(7):1505-19.
doi: 10.1039/b921842d. Epub 2010 Jan 28.

N-heterocycle construction via cyclic sulfamidates. Applications in synthesis

Affiliations

N-heterocycle construction via cyclic sulfamidates. Applications in synthesis

John F Bower et al. Org Biomol Chem. .

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.

PubMed Disclaimer

Publication types

MeSH terms

LinkOut - more resources