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Synthesis and application of chiral P,N-ligands with pseudo-meso and pseudo-C(2) symmetry
R Stranne1, J L Vasse, C Moberg
1Department of Chemistry, Organic Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden.
Organic Letters
|August 3, 2001
Abstract:
[structure: see text] Two diastereoisomeric P,N-ligands, (S,S)-1 and (R,S)-1, were synthesized and assessed in palladium-catalyzed allylic alkylations. With rac-1,3-diphenylpropenyl acetate as substrate, ligand (S,S)-1, with "pseudo-C(2)" symmetry, exhibited higher reactivity and higher enantioselectivity than the "pseudo-meso" ligand (R,S)-1, whereas reversal reactivity and selectivity were observed with rac-3-cyclohexenyl acetate.