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Synthesis 2002(6): 0766-0770
DOI: 10.1055/s-2002-25766
PAPER
© Georg Thieme Verlag Stuttgart · New York

Fluoroamines via Chiral Cyclic Sulfamidates

Jeffrey J. Posakonya, Timothy J. Tewson*b
a University of Washington, Department of Radiology Imaging Research Laboratory, Rm NW041, Box 356004, 1959 NE Pacific St., Seattle, WA 98195, USA
b University of Iowa PET Imaging Center, Department of Radiology, 0911Z JPP, 200 Hawkins Drive, Iowa City, Iowa, 52242-1007, USA
Fax: (319)3536512; e-Mail: timothy-tewson@uiowa.edu;
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Publication History

Received 20 April 2001
Publication Date:
26 April 2002 (online)

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Abstract

N-benzyl [1,2,3]-oxathiazolidine 2,2-dioxides (cyclic sulfamidates) were synthesized from their corresponding β-amino alcohols and used as substrates in fluorination reactions with tetrabutylammonium fluoride (TBAF). After desulfonation of the intermediates, the N-benzyl fluoroamines were debenzylated by transfer hydrogenolysis with Pd/C to yield (S) and (R)-2-amino-1-fluoropropanes (2b and 3b, respectively, both with 95% ee). The reactions were carried out on multi-gram scale without the need for chromatographic purification of the intermediates. In the presence of carbonate, the (S)- and (R)-N-benzylfluoroamines underwent intramolecular cyclizations in which fluoride was displaced to yield cyclic carbamates 13 and 14.

Key words

fluoroamines - nucleophilic addition - cyclizations - cyclic sulfamidates - beta-adrenergic ligands