10.1002/anie.201806343
Angewandte Chemie International Edition
COMMUNICATION
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investigate the use of proline as nucleophile. In the event,
phosphonamidate 8 was accessed in moderate yield. After
preparation
of
the
phosphonothioate 3g
from
the
phosphonate 1k,
displacement
of
the
bromide
with
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N-phenylpiperazine
yielded 9,
a
compound
exhibiting
hypotensive activity.[16] Furthermore, we prepared the
phosphinate 5i as a patented precursor to a phosphate transport
inhibitor.[17] Finally, we showed that the nosyl group on the
phosphonamidate 4a could be efficiently cleaved in classical
conditions to yield the deprotected compound 10 (Scheme 5c).
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However, the addition of aliphatic alcohols appeared to be limited to
phenylphosphonates on simple substrates. Moreover, the authors
reported in the Supporting Information that nucleophiles such as
amines or thiols were unsuccessful with their method.
Acknowledgements
We are thankful to the ERC (CoG VINCAT), the FWF (P 30266
to N.M. and M0247 to A.P.) and the DFG (Grant MA 4861/2-1)
for supporting this work. The University of Vienna is gratefully
acknowledged for continued generous support of our research
programs.
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Keywords: phosphonate • phosphonamidate •
phosphonothioate • phosphinate • triflic anhydride •
chemoselectivity
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