Cart
Letter
Phosphinamide-Directed Benzylic Lithiation. Application to the Synthesis of Peptide Building Blocks
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Section:Abstract
N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with t-BuLi in diethyl ether at low temperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowed installation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P−N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino acids.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 6 ACS Journal articles (5 most recent appear below).
One-Pot Stereoselective Synthesis of 1,2-Amino Alcohol Derivatives
Alicia Boto and Iván Romero-EstudilloOrganic Letters2011 Article ASAPOne-Pot Stereoselective Synthesis of 1,2-Amino Alcohol Derivatives
Alicia Boto and Iván Romero-EstudilloOrganic Letters2011 Article ASAPCommon β-hydroxy amino acids (such as threonine) can be readily transformed into 1,2-amino alcohols with excellent stereoselectivity. This one-pot decarboxylation–alkylation process allows the replacement of the carboxyl group by alkyl, allyl, or aryl ...
Enantioselective Synthesis of Homoallylic Amines through Reactions of (Pinacolato)allylborons with Aryl-, Heteroaryl-, Alkyl-, or Alkene-Substituted Aldimines Catalyzed by Chiral C1-Symmetric NHC−Cu Complexes
Erika M. Vieira, Marc L. Snapper, and Amir H. HoveydaJournal of the American Chemical Society2011 133 (10), 3332-3335Enantioselective Synthesis of Homoallylic Amines through Reactions of (Pinacolato)allylborons with Aryl-, Heteroaryl-, Alkyl-, or Alkene-Substituted Aldimines Catalyzed by Chiral C1-Symmetric NHC−Cu Complexes
Erika M. Vieira, Marc L. Snapper, and Amir H. HoveydaJournal of the American Chemical Society2011 133 (10), 3332-3335A catalytic method for enantioselective synthesis of homoallylamides through Cu-catalyzed reactions of stable and easily accessible (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkenyl-substituted N-phosphinoylimines is disclosed. ...
Solution and Computed Structure of o-Lithium N,N-Diisopropyl-P,P-diphenylphosphinic Amide. Unprecedented Li−O−Li−O Self-Assembly of an Aryllithium
Ignacio Fernández, Pascual Oña-Burgos, Josep M. Oliva and Fernando López OrtizJournal of the American Chemical Society2010 132 (14), 5193-5204Solution and Computed Structure of o-Lithium N,N-Diisopropyl-P,P-diphenylphosphinic Amide. Unprecedented Li−O−Li−O Self-Assembly of an Aryllithium
Ignacio Fernández, Pascual Oña-Burgos, Josep M. Oliva and Fernando López OrtizJournal of the American Chemical Society2010 132 (14), 5193-5204The structural characterization of an ortho-lithiated diphenylphosphinic amide is described for the first time. Multinuclear magnetic resonance (1H, 7Li, 13C, 31P) studies as a function of temperature and concentration employing 1D and 2D methods showed ...
Enantioselective Desymmetrization of Diphenylphosphinamides via (−)-Sparteine-Mediated Ortho-Lithiation. Synthesis of P-Chiral Ligands
Cristinel Popovici, Pascual Oña-Burgos, Ignacio Fernández, Laura Roces, Santiago García-Granda, María José Iglesias and Fernando López OrtizOrganic Letters2010 12 (3), 428-431Enantioselective Desymmetrization of Diphenylphosphinamides via (−)-Sparteine-Mediated Ortho-Lithiation. Synthesis of P-Chiral Ligands
Cristinel Popovici, Pascual Oña-Burgos, Ignacio Fernández, Laura Roces, Santiago García-Granda, María José Iglesias and Fernando López OrtizOrganic Letters2010 12 (3), 428-431Asymmetric ortho-lithiation of N-dialkyl-P,P-diphenylphosphinamides using [n-BuLi·(−)-sparteine] is described as an efficient method for the synthesis of P-chiral ortho-functionalized derivatives in high yields and ee’s from 45 to >99%. The method ...
Dearomatizing Anionic Cyclization of Phosphonamides. A Route to Phosphonic Acid Derivatives with Antitumor Properties
Gloria Ruiz-Gómez, Andrés Francesch, María José Iglesias, Fernando López-Ortiz, Carmen Cuevas and Manuel Serrano-RuizOrganic Letters2008 10 (18), 3981-3984Dearomatizing Anionic Cyclization of Phosphonamides. A Route to Phosphonic Acid Derivatives with Antitumor Properties
Gloria Ruiz-Gómez, Andrés Francesch, María José Iglesias, Fernando López-Ortiz, Carmen Cuevas and Manuel Serrano-RuizOrganic Letters2008 10 (18), 3981-3984Deprotonation of bis(N-benzyl-N-methyl)-P-arylphosphonic diamides with s-BuLi in THF at −90 °C takes place selectively at the benzylic position. The anions undergo intramolecular attack to the P-aryl ring leading to dearomatized species that were ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue February 21, 2008
- Received November 20, 2007
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
