03.08.2018

Publications

2018

83. Kärki, K.; Siitonen, J. H.; Kortet, S.; Cederström, M.; Pihko, P. M.* 'Enzymatic Resolution of 3-oxodicyclopentadiene on a Decagram Scale' Synlett, 201829, 1723-1728.

2017

82. Földes, T.; Madarász, A.; Révész, Á.; Dobi, Z.; Varga, S.; Hamza, A.; Nagy, P. R.; Pihko, P. M.; Pápai, I.* 'Stereocontrol in Diphenylprolinol Silyl Ether Catalyzed Michael Additions: Steric Shielding or Curtin-Hammett Scenario?' J. Am. Chem. Soc. 2017, 139(7), 17052–17063.

81. Neuvonen, A. J.; Földes, T.; Madarász, Á.; Pápai, I.*; Pihko, P. M.* 'Organocatalysts Fold to Generate an Active Site Pocket for the Mannich Reaction.' ACS Catalysis, 2017, 7(5), 3284–3294.

80. Mäkinen, M E.; Mallik, R.; Siitonen, J. H., Kärki, K., Pihko, P. M.* 'Towards Waltheriones C and D: Synthesis of the Oxabicyclic Core'. Synlett2017, 18, 1209–1213. Featured on the cover of Synlett 10/2017.

79. Tuokko, S.; Honkala, K.*; Pihko, P. M.* 'Pd/C Catalyzed Hydrosilylation of Enals and Enones with Triethylsilane: Conformer Populations Control the Stereoselectivity.' ACS Catalysis, 2017, 7, 480–493.

2016

78. Vijayan, A.; Baiju, T. V.; Jiiy, E.; Prakash, P.; Shimi, M.; Joseph, N.; Pihko, P. M.; Varughese, S.; Radhakrishnan, K. V.* 'An easy access to fused chromanones via rhodium catalyzed oxidative coupling of salicylaldehydes with heterobicyclic olefins.' Tetrahedron, 201672, 4007–4015.

77. Tuokko, S.; Pihko, P. M.* 'Palladium on Charcoal Catalyzed 3,4-Hydroperoxidation of β-Substituted Enals with Triethylsilane and Water.' Synlett 2016, 27, 1649–1652.

76. Suhonen, A.; Kortelainen, M.; Nauha, E.; Yliniemelä-Sipari, S.; Pihko, P. M.; Nissinen, M.* 'Conformational Properties and Folding Analysis of a Series of Seven Oligoamide Foldamers.' Cryst. Eng. Comm., 2016, 18, 2005–2013.

75. Tuokko, S.; Pihko, P. M.; Honkala, K.* 'First Principles Calculations for Hydrogenation of Acrolein on Pd and Pt: Chemoselectivity Depends on Steric Effects on the Surface.' Angew. Chem. Int. Ed. 2016, 55, 1670–1674. (VIP paper).

74. Claraz, A.; Sahoo, G.; Berta, D.; Madarász, Á.; Pápai, I.; Pihko, P. M.* 'A catalyst designed for the enantioselective construction of methyl- and alkyl-substituted tertiary stereocentres.' Angew. Chem. Int. Ed. 2016, 55, 669–673. Highlighted in Synfacts 2016, 12(2), 198.

73.  Claraz, A.; Siitonen, J. H..; Pihko, P. M.* Chapter 16 'Iminium catalysis.' In: Lewis Base Catalysis in Organic Synthesis, Vol 2.; Vedejs, E.; Denmark S. (Ed.), Wiley-VCH 2016.

2015

72. Onwukwe, G.U., Koski, M. K., Pihko, P., Schmitz, W. & Wierenga, R. K.* 'Structures of yeast peroxisomal Δ3, Δ2-enoyl-CoA isomerase complexed with acyl-CoA substrate analogues: the importance of hydrogen-bond networks for the reactivity of the catalytic base and the oxyanion hole'. Acta. Cryst. 2015, D71, 2178–2191.

71. Kortelainen, M.; Suhonen, A.; Hamza, A.; Pápai, I.;* Nauha, E.; Yliniemelä-Sipari, S.; Nissinen, M.;* Pihko, P. M.* 'Folding Patterns in a Family of Oligoamide Foldamers'. Chem. Eur. J. 2015, 21, 9493–9504.

2014

70. Tuokko, S.; Pihko, P. M.* 'Palladium on Charcoal as a Catalyst for Stoichiometric Chemo- and Stereoselective Hydrosilylations and Hydrogenations with Triethylsilane'. Org. Process Res. Dev. 2014, 18, 1740–1751.

69. Neuvonen, A. J.; Pihko, P. M.* 'Enantioselective Mannich Reaction of β-Keto Esters with Aromatic and Aliphatic Imines Using a Cooperatively Assisted Bifunctional Catalyst'. Org. Lett. 2014, 16, 5152–5155.

68. Al-Hunaiti, A.; Räisänen, M.; Pihko, P.; Leskelä, M.; Repo, T.* 'Organocatalytic Oxidation of Secondary Alcohols Using 1,2-Di(1-naphthyl)-1,2-ethanediamine (NEDA)'. Eur. J. Org. Chem. 2014, 6141–6144.

67. Siitonen, J. H., Pihko, P. M.* 'Total Synthesis of (+)-Greek Tobacco Lactone'. Synlett 2014, 25, 1888–1890.

66. Kemppainen, E. K.; Sahoo, G.; Piisola, A.; Hamza, A.; Kótai, B.; Pápai, I.*; Pihko, P. M.* 'Mukaiyama–Michael Reactions with trans-2,5-Diarylpyrrolidine Catalysts: Enantioselectivity Arises from Attractive Noncovalent Interactions, Not from Steric Hindrance'. Chem. Eur. J. 2014, 20, 5983–5993.

65. Leskinen, M. V.; Madarász, A.; Yip, K.-T.; Vuorinen, A.; Pápai, I.*; Neuvonen A. J.; Pihko, P. M.*; 'Cross-Dehydrogenative Couplings between Indoles and β-Keto Esters: Ligand-Assisted Ligand Tautomerization and Dehydrogenation via a Proton-Assisted Electron Transfer to Pd(II)'. J. Am. Chem. Soc. 2014, 136, 6453–6462.

64. Moilanen, J.*; Neuvonen, A.; Pihko, P. M.*; 'Reaction Mechanism of an Intramolecular Oxime Transfer Reaction: A Computational Study'. J. Org. Chem. 2014, 79, 20062014.

2013

63. Joseph, N.; Rajan, R.; John, J.; Devika, N. V.; Chand, S. S.; Suresh, E.; Pihko, P. M.; Radhakrishnan, K. V.*; 'An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via palladium catalyzed ring opening of azabicyclic olefins with aryl halides'. RSC Advances 2013, 3, 7751–7757.

62. Jijy, E.; Prakash, P.; Shimi, M.; Petri, P. M.; Joseph, N.; Radhakrishnan, K. V.*; 'Rhodium catalyzed oxidative coupling of salicylaldehydes with azabicyclic olefins: A one pot strategy involving aldehyde C–H cleavage and π-allyl chemistry to access fused ring chromanones'. Chem Commun. 2013, 49, 7349–7351.

61. Jijy, E.; Prakash, P.; Shimi, M.; Saranya, S.; Preethanuj, P.; Pihko, P. M.; Varughese, S.; Radhakrishnan, K. V.*; 'Rhodium (III)-catalyzed ring-opening of strained olefins through C–H activation of O-acetyl ketoximes: An efficient synthesis of trans-functionalized cyclopentenes and spiro[2.4]heptenes'. Tetrahedron Lett. 2013, 52, 7127.

60. Prakash, P.; Jijy, E.; Preethanuj, P.; Pihko, P. M.; Radhakrishnan, K. V.*; 'Palladium Catalyzed Skeletal Rearrangement of Spirotricyclic Olefins: A Facile One Pot Strategy for the Synthesis of a Novel Motif with Cyclopentene Fused to Benzofuran and Pyrazolidine'. Chem. Eur. J. 2013, 19, 10473.

59. Nimje, R. Y.; Leskinen, M. V.; Pihko, P. M.* 'Three-Component Palladium-Catalyzed Oxidative C–C Coupling Reaction: A Domino Process in Two Dimensions'. Angew. Chem. Int. Ed. 2013, 52, 4818-4822.

2012

58. Sahoo, G.; Rahaman, H.; Madarász, Á.; Pápai, I.*; Melarto, M.; Valkonen, A.; Pihko, P. M.* 'Dihydrooxazine Oxides as Key Intermediates in Organocatalytic Michael Reactions of Aldehydes to Nitroalkenes'. Angew. Chem. Int. Ed. 2012, 51, 13144-13148 (VIP paper).

57. Yip, K.-T.; Nimje, R. Y.; Leskinen, M. V.; Pihko, P. M.* 'Palladium-Catalyzed Dehydrogenative β'-Arylation of β-Keto Esters under Aerobic Conditions: Interplay of Metal and Bronsted Acids'. Chem. Eur. J. 2012, 18, 12590-12594.

56. Probst, N.; Madarász, Á.; Valkonen, A.; Pápai, I.; Rissanen, K.; Neuvonen, A.; Pihko, P. M.* 'Cooperative Assistance in Bifunctional Organocatalysis: Enantioselective Mannich Reactions with Aliphatic and Aromatic Imines. ' Angew. Chem. Int. Ed. 2012, 51, 8495-8499.

55. Himanen, J. A.; Pihko, P. M.* ' Synthesis of Trisaccharides by Hetero-Diels-Alder Welding of Two Monosaccharide Units'. Eur. J. Org. Chem. 2012, 3765-3780.

54. Leskinen, M. V.; Yip, K.-T.; Valkonen, A.; Pihko, P. M.* ' Palladium-Catalyzed Dehydrogenative Beta'-Functionalization of Beta-Keto Esters with Indoles At Room Temperature'. J. Am. Chem. Soc. 2012, 134, 5750-5753.

53. Kemppainen, E. K.; Sahoo, G.; Valkonen, A.; Pihko, P. M.* 'Mukaiyama-Michael Reactions with Acrolein and Methacrolein: A Catalytic Enantioselective Synthesis of the C17-C28 Fragment of Pectenotoxins'. Org. Lett. 2012, 14, 1086-1089.

2011

52. Yliniemelä-Sipari, S. M.; Piisola, A.; Pihko, P. M. 'Enamine Catalysis of Intermolecular Aldol Reactions (Aldehydes, Ketones).' In: Science of Synthesis: Asymmetric Organocatalysis, Vol 1.; List, B. (Ed.), Thieme, Stuttgart, 2011.

51. Pihko, P. M.;* Rahaman, H., 'Bifunctional Acid-Base Catalysts.' In: Enantioselective Organocatalyzed Reactions 1, R. Mahrwald (Ed.), Springer, Heidelberg 2011, pp. 185-207.

50. R. Venkatesan, M. Alahuhta, P. Pihko, R. Wierenga, 'High resolution crystal structures of triosephosphate isomerase (TIM) complexed with its suicide inhibitors: the conformational flexibility of the catalytic glutamate in its closed, liganded active site'. Protein Science, 2011, 20, 1387-1397. DOI: 10.2002/pro.667

49. Rahaman, H.; Madarász, Á.; Pápai, I.; Pihko, P. M.* 'Dual Hydrogen Bond - Enamine Catalysis Enables a Direct Enantioselective Three-Component Domino Reaction'. Angew. Chem. Int. Ed. 2011, 50, 6123-6127.

48. Benohoud, M.; Tuokko, S.; Pihko, P. M.* 'Stereoselective Hydrosilylation of Enals and Enones Catalyzed by Palladium Nanoparticles'. Chem. Eur. J. 2011, 17, 8404-8413.

47. Aho, J. E.; Piisola, A.; Krishnan, K. S.; Pihko, P. M.* 'Synthetic Studies Towards Pectenotoxin-2: Synthesis of the Nonanomeric 10-epi ABCDE Ring Segment via Kinetic Spiroketalization'. Eur. J. Org. Chem. 2011, 1682-1694. DOI: 10.1002/ejoc.201001411.

46. Pápai, I.; Hamza, A.; Pihko, P. M.,* Wierenga, R. K. ‘Stereoelectronic Requirements for Optimal Hydrogen Bond Catalyzed Enolization'. Chem. Eur. J. 2011, 17, 2859-2866. DOI: 10.1002/chem.201002943.

2010 and older

45. Al-Hunaiti, A.; Niemi, T.; Sibaouih, A.; Pihko, P.; Leskelä, M.; Repo, T. 'Solvent free oxidation of primary alcohols and diols using thymine iron(III) catalyst'. Chem. Commun. 2010, 46, 9250-9252

44. Yliniemelä-Sipari, S. M.; Pihko, P. M. 'Direct Aldol Reactions.' In: Science of Synthesis: Stereoselective Synthesis, Vol 2.; Molander, G. (Ed.), Thieme, Stuttgart, 2010; Chapter 2.13., pp. 621-676.

43. Pohjakallio, A.; Liu, J.; Pihko, P. M.*‘Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of b-Hydroxynitriles from Enals’. J. Org. Chem., 2010, 75, 6712-6715.

42. Pohjakallio, A.; Pihko, P. M.*, Laitinen, U. M. ‘Synthesis of 2-Isoxazolines: Enantioselective and racemic methods based on conjugate additions of oximes’. Chem. Eur. J. 2010, 16, 11325-11339.

41. Benohoud, M.; Erkkilä, A.; Pihko, P. M.* 'Organocatalytic a-Methylenation of Aldehydes: Preparation of 3,7-dimethyl-2-methylene-6-octenal'. Org. Synth. 2010, 87, 201-208.

40. Evanno, L.; Ormala, J.; Pihko, P. M.* ‘A highly enantioselective access to tetrahydro-isoquinoline and β-carboline alkaloids with simple Noyori-type catalysts in aqueous media’. Chem. Eur. J. 2009, 15, 12963-12967.

39. Pihko, P. (Ed.) ‘Hydrogen Bonding in Organic Synthesis’, Wiley-VCH, Weinheim, 2009.

38. Pihko, P. M.; Rapakko, S.; Wierenga, R. K. ‘Oxyanion Holes and Their Mimics’. In: ' Hydrogen Bonding in Organic Synthesis', Pihko, P. (Ed.), pp. 43-71, Wiley-VCH, Weinheim, 2009.

37. Pohjakallio, A. Pihko, P. M.* ’Enantioselective Synthesis of 2-Isoxazolines by an One-Flask Conjugate Addition – Oxime Transfer Process.’ Chemistry – A European Journal 2009, 15, 3960-3964.

36. Pihko, P. M.*; Majander, I.; Erkkilä, A. ’Enamine Catalysis.’ In: Topics in Current Chemistry 2009, 128, Chapter 21. DOI:10.1007/128_2008_21

35. Helmboldt, H.; Aho, J. E.; Pihko, P. M.* ’Synthetic Studies Toward Pectenotoxin 2. Part II. Synthesis of the CDE and CDEF Ring Systems.’ Org. Lett. 2008, 10, 4179-4182.

34. Aho, J. E.; Salomäki, E.; Rissanen, K.; Pihko, P. M.* ’Synthetic Studies Toward Pectenotoxin 2. Part I. Stereocontrolled Access to the C10-C22 Fragment.’ Org. Lett. 2008, 10, 4179-4182.

33. Pohjakallio, A.; Pihko, P. M.* ’A Versatile Entry to 3-Unsubstituted 2-Isoxazolines.’ Synlett 2008, 827-830.

32. Castagnolo, D.; Breuer, I.; Pihko, P. M.* ‘Direct Kinetic Formation of Nonanomeric [6.5]-Spiroketals in Aqueous Media.’ J. Org. Chem. 2007, 72, 10081-10087.

31. Erkkilä, A.; Majander. I.; Pihko, P. M.* ‘Iminium Catalysis.’ Chem. Rev. 2007, 107, 5416-5470.

30. Erkkilä, A.; Pihko, P. M.* ’Rapid Organocatalytic Aldehyde-Aldehyde Condensation Reactions.’ Eur. J. Org. Chem. 2007, 4205-4216.

29. Lindfors, J.; Pihko, R.; Pihko, P.; Laine, J.; Stenius, P. ’Contamination of paper machine press fabric materials by ASA studied with a new deposition tester.’ Nord. Pulp Paper Res. J. 2007, 22, 481-487.

28. Erkkilä, A.; Pihko, P. M.*, Clarke, M.-R. ’Simple Primary Anilines as Organocatalysts for the Epoxidation of a-Substituted Acroleins.’ Adv. Synth. Catal. 2007, 349, 802-806.

27. Lahtinen, P.; Ahmad, J. U.; Lankinen, E. Pihko, P. M.; Leskelä, M.; Repo, T. ’Organocatalyzed Oxidation of Alcohols with Molecular Oxygen.’ J. Mol. Cat. A 2007, 275, 228-232.

26. Erkkilä, A.; Pihko, P. M.* ’Mild Organocatalytic a-Methylenation of Aldehydes.’ J. Org. Chem. 2006, 71, 2538-2541.

25. Nicolaou, K. C.; Chen, D. Y.-K.; Li, Y.; Uesaka, N.; Petrovic, G.; Koftis, T. V.; Bernal, F.; Frederick, M. O.; Govindasamy, M.; Ling, T.; Pihko, P. M.; Tang, W.; Vyskocil, S. ‘Total Synthesis and Structural Elucidation of Azaspiracid-1. Synthesis-Based Analysis of Originally Proposed Structures and Indication of Their Non-Identity to the Natural Product.‘ J. Am. Chem. Soc. 2006, 128, 2258-2267.

24. Nicolaou, K. C.; Pihko, P. M.; Bernal, F.; Frederick, M. O.; Qian, W.; Uesaka, N.; Diedrichs, N.; Hinrichs, J.; Koftis, T. V.; Loizidou, E.; Petrovic, G.; Rodriquez, M.; Sarlah, D.; Zou, N. ‘Total Synthesis and Structural Elucidation of Azaspiracid-1. Construction of Key Building Blocks for Originally Proposed Structure.’ J. Am. Chem. Soc. 2006, 128, 2244-2257.

23. Pihko, P. M.* ’Enantioselective a–Fluorination of Carbonyl Compounds: Organocatalysis or Metal Catalysis?’ Angew. Chem. Int. Ed. 2006, 45, 544-547.

22. Pihko, P. M.;* Laurikainen, K. M.; Usano, A.; Nyberg, A. I.; Kaavi, J. A. ’The effect of additives on the proline-catalyzed ketone-aldehyde aldol reactions.’ Tetrahedron 2006, 62, 317-328.

21. Aho, J. E.; Pihko, P. M.;* Rissa, T. K. ’Nonanomeric Spiroketals: Structures, Sources, and Synthetic Strategies.’ Chem. Rev. 2005, 105, 4406-4440.

20. Pihko, P. M.* ’Breakthroughs in Enantioselective Brønsted Acid and Brønsted Base Catalysis.’ Lett. Org. Chem. 2005, 2, 398-403.

19. Kallström, S.; Erkkilä, A.; Pihko, P. M.;* Sjöholm, R.; Sillanpää, R.; Leino, R. ‘Consecutive Proline-Catalyzed Aldol and Metal-Mediated Allylation Reactions: Rapid Entries to Polypropionates.’ Synlett 2005, 751-756.

18. Piispanen, P. S.; Pihko, P. M.* ’Direct Synthesis of N-Substituted Aspartic Acids Using Alkali Maleates and Amines.’ Tetrahedron Lett. 2005, 46, 2751-2755.

17. Pihko, P. M.*, Rissa, T. K.; Aksela, R. ’Enantiospecific synthesis of isomers of AES, a new environmentally friendly chelating agent.’ Tetrahedron 2004, 60, 10949-10954.

16. Pihko, P. M.*; Aho, J. E. ’Access to Both Anomers of Pectenotoxin Spiroketals by Kinetic Spiroketalization.’ Org. Lett. 2004, 6, 3849-3852.

15. Pihko, P. M.;* Pohjakallio, A. ’Enantioselective Organocatalytic Asymmetric Diels Aminations: a-Aminations of Cyclic β-Keto Esters and β-Keto Lactones with Cinchonine and Cinchonidine.’ Synlett 2004, 2115-2118.

14. Nyberg, A. I.; Usano, A.; Pihko, P. M.* ’Proline-Catalyzed Ketone-Aldehyde Aldol Reactions Are Accelerated by Water.’ Synlett 2004, 1891-1896.

13. Pihko, P. M.* ’Activation of Carbonyls by Double Hydrogen Bonding: An Emerging Tool in Asymmetric Catalysis.’ Angew. Chem. Int. Ed. 2004, 43, 2062-2064.

12. Pihko, P. M.;* Erkkilä, A. ’Enantioselective synthesis of prelactone B using a proline-catalyzed crossed-aldol reaction.’ Tetrahedron Lett. 2003, 44, 7607-7609.

11. Pihko, P. M.;* Salo, T. M. ’Excess sodium ions improve Z selectivity in Horner-Wadsworth-Emmons olefinations with the Ando phosphonate.’ Tetrahedron Lett. 2003, 44, 4361-4364.

10. Selkälä, S.; Tois, J.; Pihko, P. M.;* Koskinen, A. M. P. ’Asymmetric Organocatalytic Diels-Alder Reactions on Solid Support.’ Adv. Synth. Catal. 2002, 344, 941-945.

9. Nicolaou, K. C.; Qian, W.; Bernal, F.; Uesaka, N.; Pihko, P. M.; Hinrichs, J. ‘Synthesis of the ABCD Ring System of Azaspiracid.’ Angew. Chem. Int. Ed. 2001, 40, 4068-4071.

8. Nicolaou, K. C.; Pihko, P. M.; Diedrichs, N.; Zou, N.; Bernal, F. ‘Synthesis of the FGHI Ring System of Azaspiracid.’ Angew. Chem. Int. Ed. 2001, 40, 1262-1265.

7. Pihko, P. M.; Koskinen, A. M. P. ‘The Triumph of Zinc: A Short and Highly Efficient Synthesis of the Calyculin C1-C9 Tetraene Building Block by Negishi Coupling.’ Synlett 1999, 1966-1968.

6. Pihko, P. ’Chemistry and Biology of the Calyculins.’ Acta Univ. Oul., Ser. A. (Sci. Rer. Nat.), 325. University of Oulu, Finland, 1999 (Ph. D. Dissertation).

5. Koskinen, A.M.P.; Pihko, P. M. 'Chemistry and Biology of Calyculin C.' In: Current Trends in Organic Synthesis, C. Scolastico and F. Nicotra (Eds.), Kluwer Academic/Plenum Publishers, New York, 1999, pp. 291-298.

4. Pihko, P. M.; Koskinen, A. M. P.; Nissinen, M. J.; Rissanen, K. ‘Formation of Stable [4.4] Ortho Ester Aminals During the Synthesis of C26-C32 Oxazole Fragment of Calyculin C.’ J. Org. Chem. 1999, 64, 652-654.

3. Pihko, P. M.; Koskinen, A. M. P. ‘Synthesis of the C26-C32 Oxazole Fragment of Calyculin C: A Test Case for Oxazole Syntheses.’ J. Org. Chem. 1998, 63, 92-98.

2. Lindvall, M. K.; Pihko, P. M.; Koskinen, A. M. P. ‘The Binding Mode of Calyculin A to Protein Phosphatase-1. A Novel Spiroketal Vector Model.’ J. Biol. Chem. 1997, 272, 23312-23316.

1. Koskinen, A. M. P. and Pihko, P. M. ‘Calyculins. Synthesis of the C26-C32 –fragment.’ Tetrahedron Lett. 1994, 35, 7417-7420.

*) Corresponding author.