ChemComm
Communication
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Scheme 1 Transformations of the reaction products.
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Scheme 2 ORTEP diagram of the X-ray diffraction structure of product 5.
transformations to provide other optical active derivatives
of a-fluoroalkylphosphonate.
¨
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Roschenthaler, V. Kukhar, J. Barten, N. Gvozdovska, M. Belik and
In conclusion, we have achieved Pd-catalyzed AAA of a-fluoro-
alkylphosphonate with monosubstituted allylic substrates, providing
products with two chiral centers in high yields with excellent regio-,
diastereo-, and enantioselectivities. The resulting products contain
two adjacent stereogenic centers and three functional groups
that can be easily elaborated to more complex products. Further
investigations to extend the reaction scope and applications of
this methodology in organic synthesis are in progress.
This work was financially supported by the Major Basic
Research Development Program (2010CB833300), National Natural
Science Foundation of China (21121062, 21302205, 21032007),
Chinese Academy of Sciences and the Technology Commission
of Shanghai Municipality. This communication is dedicated to
Professor Chang Tao Qian on the occasion of his 80th birthday.
A. Sorochinsky, Tetrahedron Lett., 2004, 45, 6665.
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12 Some examples of Pd-catalyzed AAA using fluoro-containing nucleo-
philes: (a) J. T. Mohr, D. C. Behenna, A. M. Harned and B. M. Stoltz,
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