Synthesis and application of chiral P,N-ligands with pseudo-meso and pseudo-C-2 symmetry

Authors
Stranne, R Vasse, JL Moberg, C
Citation
R. Stranne et al., Synthesis and application of chiral P,N-ligands with pseudo-meso and pseudo-C-2 symmetry, ORG LETT, 3(16), 2001, pp. 2525-2528
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
16
Year of publication
2001
Pages
2525 - 2528
Database
ISI
SICI code
1523-7060(20010809)3:16<2525:SAAOCP>2.0.ZU;2-#
Abstract
[GRAPHICS] Two diastereoisomeric P,N-ligands, (S,S)-1 and (R,S)-1, were synthesized an d assessed in palladium-catalyzed allylic alkylations. With rac-1,3-dipheny lpropenyl acetate as substrate, ligand (AS)-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 obse rved with rac-3-cyclohexenyl acetate.