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2005
Organo-phosphorus compounds
S 0080
Copper-Catalyzed, Enantioselective Desymmetrization of meso Cyclic Allylic
phosphates) with Organozinc Reagents. — A highly regio-, diastereo27- 166 Bis(diethyl
and enantioselective desymmetrization of five-, six- , or seven-membered cyclic meso-bis(phosphates) is presented. It involves their copper-catalyzed reaction with organozinc reagents in the presence of two different classes of chiral ligands, namely Schiff
bases (I) or BINOL-derived phosphoramidites (II), (III). The optimum conditions have
to be found for each single substrate. In general, however, the Schiff base ligands (I)
are more suitable for the desymmetrization of five-membered cyclic meso-bis(phosphates) while phosphoramidite ligands give better yields for six- or seven-membered
cyclic bis(phosphates). — (PIARULLI*, U.; DAUBOS, P.; CLAVERIE, C.; MONTI,
C.; GENNARI, C.; Eur. J. Org. Chem. 2005, 5, 895-906; Dip. Sci. Chim. Ambientali,
Univ. Insubria, I-22100 Como, Italy; Eng.) — Mischke
2005
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