P-Chirogenic Diaminophosphine Oxide: A New Class of Chiral Phosphorus Ligands for Asymmetric Catalysis
- 1 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (12) , 3690-3691
- https://doi.org/10.1021/ja031792a
Abstract
We successfully synthesized a novel P-chirogenic diaminophosphine oxide 4, which was applied to catalytic enantioselective construction of quaternary carbon centers using Pd-catalyzed asymmetric allylic substitution with various β-keto esters (up to 99% yield, 94% ee). Preliminary mechanistic studies indicated that two molecules of 8 coordinate to the Pd metal in a monodentate fashion, resulting in the formation of Pd complex 9 (Pd:8 = 1:2), which functions as the active species.Keywords
This publication has 18 references indexed in Scilit:
- Highly Active, Air-Stable Palladium Catalysts for the C−C and C−S Bond-Forming Reactions of Vinyl and Aryl Chlorides: Use of Commercially Available [(t-Bu)2P(OH)]2PdCl2, [(t-Bu)2P(OH)PdCl2]2, and [[(t-Bu)2PO···H···OP(t-Bu)2]PdCl]2 as CatalystsThe Journal of Organic Chemistry, 2002
- Enantioselective Allylations of Azlactones with Unsymmetrical Acyclic Allyl EstersJournal of the American Chemical Society, 1999
- Catalytic Asymmetric Allylation of Prochiral Nucleophiles, α-Acetamido-β-ketoestersJournal of the American Chemical Society, 1999
- Asymmetric Alkylation of β-KetoestersJournal of the American Chemical Society, 1997
- Chiral phosphine ligands modified by crown ethers: an application to palladium-catalyzed asymmetric allylation of .beta.-diketonesJournal of the American Chemical Society, 1992
- Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. 5. Palladium-catalyzed asymmetric allylation of active methine compoundsThe Journal of Organic Chemistry, 1988
- FORMATION OF COORDINATEDt-Bu2P(H)OviaREACTION OFt-Bu2PCI WITH ETHANOLIC ReO4−. SYNTHESIS AND STRUCTURE OFtrans-ReOCl2(OEt){t-Bu2P(OEt)}{t-Bu2P(H)O}Journal of Coordination Chemistry, 1987
- New chiral ligands designed for palladium-catalysed asymmetric allylic alkylationJournal of the Chemical Society, Chemical Communications, 1982
- Diphenylphosphinato- and Hydroxydiphenylphosphine Complexes of Platinum(II) and Palladium(II)Canadian Journal of Chemistry, 1971
- Amino-acids and peptides. Part XII. α- and β-L-aspartyl-L-valineJournal of the Chemical Society, 1954