CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2007, Vol. 79, No. 12, pp. 2217-2227

http://dx.doi.org/10.1351/pac200779122217

H-Phosphonates: Versatile synthetic precursors to biologically active phosphorus compounds*

Adam Kraszewski1 and Jacek Stawinski1,2

1 Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznan, Poland
2 Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-10691 Stockholm, Sweden

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Khemchyan Levon L., Ivanova Julia V., Zalesskiy Sergey S., Ananikov Valentine P., Beletskaya Irina P., Starikova Zoya A.: Unprecedented Control of Selectivity in Nickel-Catalyzed Hydrophosphorylation of Alkynes: Efficient Route to Mono- and Bisphosphonates. Adv. Synth. Catal. 2014, 356, 771. <http://dx.doi.org/10.1002/adsc.201400123>
  • Wang Tao, Sang Shuai, Liu Liu, Qiao Hongwei, Gao Yuxing, Zhao Yufen: Experimental and Theoretical Study on Palladium-Catalyzed C–P Bond Formation via Direct Coupling of Triarylbismuths with P(O)–H Compounds. J. Org. Chem. 2014, 79, 608. <http://dx.doi.org/10.1021/jo402392t>
  • Uehara Sho, Hiura Shingo, Higashida Renpei, Oka Natsuhisa, Wada Takeshi: Solid-Phase Synthesis of P-Boronated Oligonucleotides by the H-Boranophosphonate Method. J. Org. Chem. 2014, 140328152859005. <http://dx.doi.org/10.1021/jo500185b>
  • Liu Liu, Lv Ye, Wu Yile, Gao Xiang, Zeng Zhiping, Gao Yuxing, Tang Guo, Zhao Yufen: Experimental and theoretical studies on nickel–zinc-catalyzed cross-coupling of gem-dibromoalkenes with P(O)–H compounds. RSC Adv. 2014, 4, 2322. <http://dx.doi.org/10.1039/c3ra45212c>
  • Shankar Ravi, Asija Meenal, Singla Nisha, -Köhn Gabriele Kociok, Molloy Kieran C: Synthesis, characterization and hydrolytic stability of diorganotin(IV)bis(O-alkyl alkylphosphonate)s. Can. J. Chem. 2014, 140224143410008. <http://dx.doi.org/10.1139/cjc-2013-0486>
  • Piergies Natalia, Proniewicz Edyta: Structure Characterization of [N-Phenylamino(2-boronphenyl)-R-methyl]phosphonic Acid by Vibrational Spectroscopy and Density Functional Theory Calculations. Journal of Spectroscopy 2014, 2014, 1. <http://dx.doi.org/10.1155/2014/247237>
  • Sun Qi, Yang Qingkun, Gong Shanshan, Fu Quanlei, Xiao Qiang: Synthesis and enzymatic evaluation of phosphoramidon and its β anomer: Anomerization of α-l-rhamnose triacetate upon phosphitylation. Bioorganic & Medicinal Chemistry 2013, 21, 6778. <http://dx.doi.org/10.1016/j.bmc.2013.07.052>
  • Kotlarska Justyna, Binnemans Koen, Dehaen Wim: A convenient two-step synthesis of dialkylphosphate ionic liquids. Tetrahedron 2013, 69, 9947. <http://dx.doi.org/10.1016/j.tet.2013.09.074>
  • Feng Chen-Guo, Ye Mengchun, Xiao Kai-Jiong, Li Suhua, Yu Jin-Quan: Pd(II)-Catalyzed Phosphorylation of Aryl C–H Bonds. J. Am. Chem. Soc. 2013, 135, 9322. <http://dx.doi.org/10.1021/ja404526x>
  • Ferry Angélique, Malik Gaëlle, Retailleau Pascal, Guinchard Xavier, Crich David: Alternative Synthesis of P-Chiral Phosphonite-Borane Complexes: Application to the Synthesis of Phostone–Phostone Dimers. J. Org. Chem. 2013, 78, 6858. <http://dx.doi.org/10.1021/jo400864s>
  • Prasan Ojha Devi, Ramaiah Prabhu Kandikere: Pd-Catalyzed Cross-Coupling Reactions of Hydrazones: Regioselective Synthesis of Highly Branched Dienes. J. Org. Chem. 2013, 78, 12136. <http://dx.doi.org/10.1021/jo402153t>
  • Wang Guan-Nan, Lau Pui Sai, Li Yingfu, Ye Xin-Shan: Synthesis and evaluation of glucosamine-6-phosphate analogues as activators of glmS riboswitch. Tetrahedron 2012, 68, 9405. <http://dx.doi.org/10.1016/j.tet.2012.09.015>
  • Ferry Angélique, Guinchard Xavier, Retailleau Pascal, Crich David: Synthesis, Characterization, and Coupling Reactions of Six-Membered Cyclic P-Chiral Ammonium Phosphonite–Boranes; Reactive H-Phosphinate Equivalents for the Stereoselective Synthesis of Glycomimetics. J. Am. Chem. Soc. 2012, 134, 12289. <http://dx.doi.org/10.1021/ja305104b>
  • Roy Béatrice, Lefebvre Isabelle, Puy Jean-Yves, Périgaud Christian: A facile and effective synthesis of lamivudine 5′-diphosphate. Tetrahetron Lett 2011, 52, 1250. <http://dx.doi.org/10.1016/j.tetlet.2010.12.105>
  • Oka Natsuhisa, Wada Takeshi: Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms. Chemical Society Review 2011, 40, 5829. <http://dx.doi.org/10.1039/c1cs15102a>
  • Dougan Jennifer A., Reid Andrew. K., Graham Duncan: Thioctic acid modification of oligonucleotides using an H-phosphonate. Tetrahetron Lett 2010, 51, 5787. <http://dx.doi.org/10.1016/j.tetlet.2010.08.107>
  • Sobkowski Michal, Stawinski Jacek, Kraszewski Adam: Stereochemistry of Internucleotide Bond Formation by the H-Phosphonate Method. 5. The Role of Brønsted and H-Bonding Base Catalysis in Ribonucleoside H-Phosphonate Condensation—Chemical and Stereochemical Consequences. Nucleos Nucleot Nuc Acids 2010, 29, 628. <http://dx.doi.org/10.1080/15257770.2010.497014>
  • Iwamoto Naoki, Oka Natsuhisa, Sato Terutoshi, Wada Takeshi: Stereocontrolled Solid-Phase Synthesis of Oligonucleoside H-Phosphonates by an Oxazaphospholidine Approach. Angew Chem 2009, 121, 504. <http://dx.doi.org/10.1002/ange.200804408>
  • Iwamoto Naoki, Oka Natsuhisa, Sato Terutoshi, Wada Takeshi: Stereocontrolled Solid-Phase Synthesis of Oligonucleoside H-Phosphonates by an Oxazaphospholidine Approach. Angew Chem Int Ed 2009, 48, 496. <http://dx.doi.org/10.1002/anie.200804408>
  • Uraguchi Daisuke, Ito Takaki, Ooi Takashi: Generation of Chiral Phosphonium Dialkyl Phosphite as a Highly Reactive P-Nucleophile: Application to Asymmetric Hydrophosphonylation of Aldehydes. J Am Chem Soc 2009, 131, 3836. <http://dx.doi.org/10.1021/ja810043d>