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2005
Dioxane derivatives
R 0470
Asymmetric Palladium-Catalyzed Annulation of Benzene-1,2-diol and Racemic
Propargylic Carbonates Bearing Two Different Substituents. — Two
29- 161 Secondary
regioisomers are formed in the asymmetric palladium-catalyzed cyclization of catechol
with various racemic secondary propargylic carbonates in the presence of (R)-BINAP
as the chiral ligand. High enantioselectivities of the products are induced by the stereospecific protonation of intermediate palladium-carbene complexes. No reaction is
observed for substrates with tert-butyl substituents. — (DOMINCZAK, N.; DAMEZ,
C.; RHERS, B.; LABROSSE, J.-R.; LHOSTE, P.; KRYCZKA, B.; SINOU*, D.;
Tetrahedron 61 (2005) 10, 2589-2599; Lab. Synth. Asymetrique, CNRS, Ec. Sci.
Chim. Ind., Univ. Claude Bernard Lyon, F-69622 Villeurbanne, Fr.; Eng.) —
S. Adam
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