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Pure Appl. Chem., 2008, Vol. 80, No. 4, pp. 687-694

http://dx.doi.org/10.1351/pac200880040687

Stereoselectivity of the Petasis reaction with various chiral amines and styrenylboronic acids

Quentin I. Churches1, Helen E. Stewart2, Scott B. Cohen2, Adam Shröder1, Peter Turner2 and Craig A. Hutton1

1 School of Chemistry and Bio21 Institute of Molecular Science and Biotechnology, The University of Melbourne, VIC 3010, Australia
2 School of Chemistry, The University of Sydney, NSW 2006, Australia

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  • Haddad Terra, Gershman Rachel, Dilis Robert, Labaree David, Hochberg Richard B., Hanson Robert N.: Synthesis and evaluation of 4-(substituted styryl/alkenyl)-3,5-bis(4-hydroxyphenyl)-isoxazoles as ligands for the estrogen receptor. Bioorganic & Medicinal Chemistry Letters 2012, 22, 5999. <http://dx.doi.org/10.1016/j.bmcl.2012.06.097>
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  • Han Wen-Yong, Wu Zhi-Jun, Zhang Xiao-Mei, Yuan Wei-Cheng: Enantioselective Organocatalytic Three-Component Petasis Reaction among Salicylaldehydes, Amines, and Organoboronic Acids. Org Lett 2012, 14, 976. <http://dx.doi.org/10.1021/ol203109a>
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  • Crawford J. M., Portmann C., Zhang X., Roeffaers M. B. J., Clardy J.: Small molecule perimeter defense in entomopathogenic bacteria. Proceedings of the National Academy of Sciences 2012, 109, 10821. <http://dx.doi.org/10.1073/pnas.1201160109>
  • Mandai Hiroki, Suga Seiji, Murota Kyouta: Studies on the Petasis Reaction of 2-Pyridinecarbaldehyde Derivatives and Its Products. HETEROCYCLES 2012, 85, 1655. <http://dx.doi.org/10.3987/COM-12-12500>
  • Anbarasan Pazhamalai, Neumann Helfried, Beller Matthias: A General Rhodium-Catalyzed Cyanation of Aryl and Alkenyl Boronic Acids. Angew Chem 2011, 123, 539. <http://dx.doi.org/10.1002/ange.201006044>
  • Anbarasan Pazhamalai, Neumann Helfried, Beller Matthias: A General Rhodium-Catalyzed Cyanation of Aryl and Alkenyl Boronic Acids. Angew Chem Int Ed 2011, 50, 519. <http://dx.doi.org/10.1002/anie.201006044>
  • Churches Quentin I., White Jonathan M., Hutton Craig A.: Synthesis of β,γ-Dihydroxyhomotyrosines by a Tandem Petasis–Asymmetric Dihydroxylation Approach. Org Lett 2011, 13, 2900. <http://dx.doi.org/10.1021/ol200917s>
  • Churches Quentin I., Johnson James K., Fifer Nathan L., Hutton Craig A.: Anomalies in the Stereoselectivity of the Petasis Reaction Using Styrenyl Boronic Acids. Aust J Chem 2011, 64, 62. <http://dx.doi.org/10.1071/CH10341>
  • Mandai Hiroki, Murota Kyouta, Sakai Takashi: An improved protocol for Petasis reaction of 2-pyridinecarbaldehydes. Tetrahetron Lett 2010, 51, 4779. <http://dx.doi.org/10.1016/j.tetlet.2010.07.039>