H.-J. Cristau et al. / Tetrahedron Letters 42 (2001) 4491–4494
4493
solid, whereas 6c and 6d afford a viscous oil. Com-
pounds 6 were fully characterized by 31P, 1H, 13C
NMR, COSY 1H/1H, COSY 1H/13C, mass spec-
troscopy, IR and elementary analysis.
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Compounds 6a and 6b were completely deprotected by
using an excess of 47% bromhydric acid at 100°C,
affording compounds 7 in a quantitative yield as a
mixture of two diastereomers (Scheme 2).19
In order to show the value of phosphinodipeptide
analog 6 as a synthetic intermediate, selective deprotec-
tion of the various protective groups is under progress
in our laboratory.
Moreover, to check its generality, we will apply this
synthetic method to various N-diphenyl methylimines
and acrylates to obtain a large number of compounds
8.
4. McKittrick, B. A.; Stamford, A. W.; Weng, X.; Ma,
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Synthesis 1987, 942–943; (l) Jiao, X. Y.; Verbruggen,
C.; Borloo, M.; Bollaert, W.; De Groot, A.; Dommisse,
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Further, in order to avoid the separation of each
diastereoisomer 6a–d from the mixture, asymmetric
inductions will be investigated to obtain stereocontrol
in the formation of the various chiral centers,20,21
affording
stereoselectively
only
the
desired
diastereomer.
Acknowledgements
Agne`s Coulombeau is grateful to Aventis CropScience
and to the CNRS for a scholarship.
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