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Original Articles

Novel 1,3,2-diazaphospholidines with pseudodipeptide substituents

ORCID Icon, , , , , , , , , & show all
Pages 493-496 | Received 13 Sep 2018, Accepted 03 Oct 2018, Published online: 30 Dec 2018

References

  • Fernandez-Perez, H.; Etayo, P.; Panossian, A.; Vidal-Ferran, A. Phosphine-Phosphinite and Phosphine-Phosphite Ligands: Preparation and Applications in Asymmetric Catalysis. Chem. Rev. 2011, 111, 2119–2176.
  • Falciola, C. A.; Alexakis, A. Copper-Catalyzed Asymmetric Allylic Alkylation. Eur. J. Org. Chem. 2008, 2008, 3765–3780.
  • Hargaden, G. C.; Guiry, P. Recent Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis. Chem. Rev. 2009, 109, 2505–2550.
  • Börner, A. Phosphorus Ligands in Asymmetric Catalysis, Börner, A. Ed.; Wiley-VCH: Weinheim, 2008; 1546 pp.
  • Kamer, P. C. J. Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis, Kamer, P. C. J.; van Leeuwen, P. W. N. M., Eds.; Wiley-VCH: Chichester, 2012, 566 pp.
  • Teichert, J. F.; Feringa, B. L. Phosphoramidites: Privileged Ligands in Asymmetric Catalysis. Angew. Chem. Int. Ed. Engl. 2010, 49, 2486–2528.
  • van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Claver, C.; Pamies, O.; Dieguez, M. Phosphite-Containing Ligands for Asymmetric Catalysis. Chem. Rev. 2011, 111, 2077–2118.
  • Reetz, M. T.; Oka, H.; Goddard, R. Binaphthyldiamine-Based Diazaphospholidinesas a New Class of Chiral Monodentate- P-Ligands. Synthesis 2003, 12, 1809–1814.
  • Trost, B. M.; Lam, T. M. Development of Diamidophosphite Ligands and Their Application to the Palladium-Catalyzed Vinyl-Substituted Trimethylenemethane Asymmetric [3 + 2] Cycloaddition. J. Am. Chem. Soc. 2012, 134, 11319–11321.
  • Bravo, M. J.; Ceder, R. M.; Muller, G.; Rocamora, M. New Enantiopure P,P-Bidentate Bis(diamidophosphite) Ligands. Application in Asymmetric Rhodium-Catalyzed Hydrogenation. Organometallics 2013, 32, 2632–2642.
  • Gavrilov, K. N.; Zheglov, S. V.; Groshkin, N. N.; Gavrilov, V. K.; Maksimova, M. G.; Volov, A. N.; Zamilatskov, I. A. Phosphorylated (S)-Tert-Leucinol Isophthalic Diamide as a Ligand for Pd-Catalyzed Asymmetric Allylic Substitution. Russ. Chem. Bull. 2014, 63, 2635–2640.
  • Bravo, M. J.; Ceder, R. M.; Grabulosa, A.; Muller, G.; Rocamora, M.; Font-Bardia, M. Palladium Allylic Complexes with Enantiopure Bis(diamidophosphite) Ligands Bearing a Cyclohexane-1,2-Diamine Skeleton as Catalysts in the Allylic Substitution Reaction. J. Organomet. Chem. 2017, 830, 42–55.
  • Zhou, Q.-L. Privileged Chiral Ligands and Catalysts; Zhou, Q.-L., Ed.; Wiley-VCH: Weinheim, 2011; 462 pp.
  • Ohkuma, T.; Kitamura, M.; Noyori, R. Catalytic Asymmetric Synthesis, Ojima, I., Ed.; Wiley-VCH: New York, 2000; 880 pp., 1–110.
  • Crepy, K. V. L.; Imamoto, T. Recent Developments in Catalytic Asymmetric Hydrogenation Employing P‐Chirogenic Diphosphine Ligands. Adv. Synth. Catal. 2003, 345,79–101.
  • Grabulosa, A. in P-Stereogenic Ligands in Enantioselective Catalysis, Grabulosa, A. Ed.; Royal Society of Chemistry: Cambridge, 2011; 501 pp.
  • Meeuwissen, J.; Reek, J. N. H. Supramolecular Catalysis beyond Enzyme Mimics. Nat. Chem. 2010, 2, 615–621.
  • Carboni, S.; Gennari, C.; Pignataro, L.; Piarulli, U. Supramolecular Ligand-Ligand and Ligand-Substrate Interactions for Highly Selective Transition Metal Catalysis. Dalton Trans. 2011, 40, 4355–4373.
  • Bellini, R.; van der Vlugt, J. I.; Reek, J. N. H. Supramolecular Self-Assembled Ligands in Asymmetric Transition Metal Catalysis. Isr. J. Chem. 2012, 52, 613–629.
  • Raynal, M.; Ballester, P.; Vidal-Ferran, A.; van Leeuwen, P. W. N. M. Supramolecular Catalysis. Part 1: Non-Covalent Interactions as a Tool for Building and Modifying Homogeneous Catalysts. Chem. Soc. Rev. 2014, 43, 1660–1733.
  • Ohmatsu, K.; Ooi, T. Design of Supramolecular Chiral Ligands for Asymmetric Metal Catalysis. Tetrahedron Letters 2015, 56, 2043–2048.
  • Breit, B.; Laungani, A. C. Copper-Catalyzed Enantioselective Conjugate Addition of Dialkylzinc Reagents to Enones with New Peptidyl Phosphane Ligands. Tetrahedron: Asymmetry 2003, 14, 3823–3826.
  • Théveau, L.; Bellini, R.; Dydio, P.; Szabo, Z.; van der Werf, A.; Sander, R. A.; Reek, J. N. H.; Moberg, C. Cofactor-Controlled Chirality of Tropoisomeric Ligand. Organometallics 2016, 35, 1956–1963.
  • Lu, Z.; Ma, S. Metal-Catalyzed Enantioselective Allylation in Asymmetric Synthesis. Angew. Chem. Int. Ed. 2008, 47, 258–297.
  • Dieguez, M.; Pamies, O. Biaryl Phosphites: New Efficient Adaptative Ligands for Pd-Catalyzed Asymmetric Allylic Substitution Reactions. Acc. Chem. Res. 2010, 43,312–322.
  • Lafrance, D.; Bowles, P.; Leeman, K.; Rafka, R. Mild Decarboxylative Activation of Malonic Acid Derivatives by 1,1'-Carbonyldiimidazole. Org. Lett. 2011, 13, 2322–2325.
  • Trost, B. M. Pd and Mo Catalyzed Asymmetric Allylic Alkylation. Org. Process. Res. Dev. 2012, 16, 185–194.
  • Nag, S.; Batra, S. Applications of Allylamines for the Syntheses of Aza-Heterocycles. Tetrahedron 2011, 67, 8959–9061.
  • Chavan, S. P.; Khairnar, L. B.; Chavan, P. N. Efficient and Mild Method for Preparation of Allylic Amines from Aziridine-2-Alcohols Using PPh3/I2/Imidazole. Tetrahedron Lett. 2014, 55, 5905–5907.
  • Liu, Y.; Han, S.-J.; Liu, W.-B.; Stoltz, B. M. Catalytic Enantioselective Construction of Quaternary Stereocenters: Assembly of Key Building Blocks for the Synthesis of Biologically Active Molecules. Acc. Chem. Res. 2015, 48, 740–751.
  • Punirun, T.; Peewasan, K.; Kuhakarn, C.; Soorukram, D.; Tuchinda, P.; Reutrakul, V.; Kongsaeree, P.; Prabpai, S.; Pohmakotr, M. Synthesis of Gem-Difluoromethylenated Bicyclo[m.n.0]Alkan-1-Ols and Their Ring-Expansion to Gem-Difluoromethylenated Macrocyclic Lactones. Org. Lett. 2012, 14, 1820–1823.
  • Yen, V.; Szabo, W. A. Applications of Transition Metal Catalysis in Drug Discovery and Development: An Industrial Perspective, Crawley, M. L.; Trost, B. M., Eds.; Wiley-VCH: Hoboken, 2012, 376 pp., 165–213.
  • Ghosh, D.; Sadhukhan, A.; Maity, N. C.; Abdi, S. H. R.; Khan, N. H.; Kureshy, R. I.; Bajaj, H. C. Oxazoline Derivatives Tagged with Tosylated Amino Acids as Recyclable Organocatalysts for Enantioselective Allylation of Aldehydes. RSC Adv. 2014, 4, 12257–12265.
  • Gavrilov, K. N.; Chuchelkin, I. V.; Zheglov, S. V.; Gavrilov, V. K.; Novikov, I. M.; Firsin, I. D.; Shiryaev, A. A. Palladium and Rhodium-Catalyzed Enantioselective Reactions Mediated by Pseudodipeptide-Based Phosphite-Type Ligand. Russ. Chem. Bull. 2018, 67, 916–922.
  • Tsarev, V. N.; Lyubimov, S. E.; Shiryaev, A. A.; Zheglov, S. V.; Bondarev, O. G.; Davankov, V. A.; Kabro, A. A.; Moiseev, S. K.; Kalinin, V. N.; Gavrilov, K. N. P-Chiral Monodentate Diamidophosphites − New and Efficient Ligands for Palladium-Catalysed Asymmetric Allylic Substitution. Eur. J. Org. Chem. 2004, 2004, 2214–2222.
  • Brunel, J. M.; Constantieux, T.; Buono, G. A Practical Method for the Large-Scale Synthesis of Diastereomerically Pure (2R,5S)- 3-Phenyl-2-(8-Quinolinoxy)- 1,3-Diaza-2-Phosphabicyclo-[3.3.0]-Octane Ligand (QUIPHOS). Synthesis and X-Ray Structure of Its Corresponding Chiral pi-Allyl Palladium Complex. J. Org. Chem. 1999, 64, 8940–8942.
  • Barta, K.; Hölscher, M.; Franciò, G.; Leitner, W. Modular Synthesis of Novel Chiral Phosphorous Triamides Based on ( S )- N -(Pyrrolidin-2-Ylmethyl)Aniline and Their Application in Asymmetric Catalysis. Eur. J. Org. Chem. 2009, 2009, 4102–4116.

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