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P-Chirogenic Diaminophosphine Oxide: A New Class of Chiral Phosphorus Ligands for Asymmetric Catalysis
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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.
Citing Articles
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This article has been cited by 10 ACS Journal articles (5 most recent appear below).
Coordination Polymer Nanofibers Generated by Microfluidic Synthesis
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Josep Puigmartí-Luis, Marta Rubio-Martínez, Urs Hartfelder, Inhar Imaz, Daniel Maspoch, and Petra S. DittrichJournal of the American Chemical Society2011 133 (12), 4216-4219One-dimensional coordination polymer nanostructures are an emerging class of nanoscale materials with many potential applications. Here, we report the first case of coordination polymer nanofibers assembled using microfluidic technologies. Unlike common ...
Gas-Phase Study of Phenylacetylene and Norbornadiene on a Palladium(II) Phosphinous Acid Complex: Importance of the Order of Introduction of the Organic Partners
Reddy Thota, Denis Lesage, Yves Gimbert, Laurent Giordano, Stéphane Humbel, Anne Milet, Gérard Buono and Jean-Claude TabetOrganometallics2009 28 (9), 2735-2743Gas-Phase Study of Phenylacetylene and Norbornadiene on a Palladium(II) Phosphinous Acid Complex: Importance of the Order of Introduction of the Organic Partners
Reddy Thota, Denis Lesage, Yves Gimbert, Laurent Giordano, Stéphane Humbel, Anne Milet, Gérard Buono and Jean-Claude TabetOrganometallics2009 28 (9), 2735-2743Collision-activated reaction (CAR)/collision-induced dissociation (CID) mass spectral experiments were performed on the cationic Pd(II) complex (Pd(OPPhtBu)2H). Theoretical calculations combined with mass spectrometry experiments support first a change in ...
Pd-Catalyzed Asymmetric Allylic Amination of Morita−Baylis−Hillman Adduct Derivatives Using Chiral Diaminophosphine Oxides: DIAPHOXs
Tetsuhiro Nemoto, Takashi Fukuyama, Eri Yamamoto, Shinji Tamura, Tomoaki Fukuda, Takayoshi Matsumoto, Yuichi Akimoto, and Yasumasa HamadaOrganic Letters2007 9 (5), 927-930Pd-Catalyzed Asymmetric Allylic Amination of Morita−Baylis−Hillman Adduct Derivatives Using Chiral Diaminophosphine Oxides: DIAPHOXs
Tetsuhiro Nemoto, Takashi Fukuyama, Eri Yamamoto, Shinji Tamura, Tomoaki Fukuda, Takayoshi Matsumoto, Yuichi Akimoto, and Yasumasa HamadaOrganic Letters2007 9 (5), 927-930Asymmetric allylic amination of allylic carbonates prepared from racemic Morita−Baylis−Hillman adducts proceeded in the presence of Pd catalyst, chiral diaminophosphine oxide (DIAPHOX), and BSA, affording the corresponding chiral aza-Morita−Baylis−Hillman ...
Development of New P-Chiral Phosphorodiamidite Ligands Having a Pyrrolo[1,2-c]diazaphosphol-1-one Unit and Their Application to Regio- and Enantioselective Iridium-Catalyzed Allylic Etherification
Masahiro Kimura and Yasuhiro UozumiThe Journal of Organic Chemistry2007 72 (3), 707-714Development of New P-Chiral Phosphorodiamidite Ligands Having a Pyrrolo[1,2-c]diazaphosphol-1-one Unit and Their Application to Regio- and Enantioselective Iridium-Catalyzed Allylic Etherification
Masahiro Kimura and Yasuhiro UozumiThe Journal of Organic Chemistry2007 72 (3), 707-714Ten types of new P-chiral phosphorodiamidite ligands having pyrrolo[1,2-c][1,3,2]diazaphosphol-1-one backbone were designed and prepared. They were preliminarily utilized for iridium-catalyzed asymmetric allylic etherification of cinnamyl carbonate with ...
Diastereoselective Ring-Closing Metathesis: Synthesis of P-Stereogenic Phosphinates from Prochiral Phosphinic Acid Derivatives
Katherine S. Dunne, Fabrice Bisaro, Barbara Odell, Jean-Marc Paris, and Véronique GouverneurThe Journal of Organic Chemistry2005 70 (26), 10803-10809Diastereoselective Ring-Closing Metathesis: Synthesis of P-Stereogenic Phosphinates from Prochiral Phosphinic Acid Derivatives
Katherine S. Dunne, Fabrice Bisaro, Barbara Odell, Jean-Marc Paris, and Véronique GouverneurThe Journal of Organic Chemistry2005 70 (26), 10803-10809The preparation of phosphorus-containing trienes featuring two diastereotopic vinyl moieties followed by a diastereoselective ring-closing metathesis is described. This methodology allowed for the synthesis of novel highly functionalized P-stereogenic ...
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History
- Published In Issue March 31, 2004
- Received December 17, 2003
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