Novel ferrocenyl ligands with planar and central chirality in Pd-catalyzedallylic substitutions

Authors
Enders, D Peters, R Runsink, J Bats, JW
Citation
D. Enders et al., Novel ferrocenyl ligands with planar and central chirality in Pd-catalyzedallylic substitutions, ORG LETT, 1(11), 1999, pp. 1863-1866
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
11
Year of publication
1999
Pages
1863 - 1866
Database
ISI
SICI code
1523-7060(199912)1:11<1863:NFLWPA>2.0.ZU;2-1
Abstract
[GRAPHICS] The use of planar chiral ferrocenyl ligands bearing a stereogenic center in beta-position of the side chain was investigated in Pd-catalyzed enantiose lective allylic substitutions. By employing 2.2 mol % of a P,S-ligand and 1 .0 mol % of [Pd(eta(3)-C3H5)Cl](2), the alkylation of the standard test sys tem (+/-) (E)-diphenyl-2-propenyl acetate using dimethylmalonate/BSA as nuc leophile proceeded in quantitative yield with an ee of 97%, which is the be st value reported so far in this reaction using a P,S-ligand.