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Pure Appl. Chem., 2006, Vol. 78, No. 7, pp. 1389-1395

http://dx.doi.org/10.1351/pac200678071389

Asymmetric synthesis with the robust and versatile 10-substituted 9-borabicyclo[3.3.2]decanes: Homoallylic amines from aldimines

Eliud Hernandez, Eda Canales, Eduvigis Gonzalez and John A. Soderquist

University of Puerto Rico, Department of Chemistry, Rio Piedras, 00931-3346, Puerto Rico

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  • Ding Lei, Chen Jing, Hu Yifan, Xu Juan, Gong Xing, Xu Dongfang, Zhao Baoguo, Li Hexing: Aminative Umpolung of Aldehydes to α-Amino Anion Equivalents for Pd-Catalyzed Allylation: An Efficient Synthesis of Homoallylic Amines. Org. Lett. 2014, 16, 720. <http://dx.doi.org/10.1021/ol4034012>
  • Fustero Santos, Lázaro Rubén, Aiguabella Nuria, Riera Antoni, Simón-Fuentes Antonio, Barrio Pablo: Asymmetric Allylation/Pauson–Khand Reaction: A Simple Entry to Polycyclic Amines. Application to the Synthesis of Aminosteroid Analogues. Org. Lett. 2014, 16, 1224. <http://dx.doi.org/10.1021/ol500142c>
  • SUDHAKAR PAGIDI, THILAGAR PAKKIRISAMY: Ferrocene-based Lewis acids and Lewis pairs: Synthesis and structural characterization. J Chem Sci 2013, 125, 41. <http://dx.doi.org/10.1007/s12039-012-0356-8>
  • Martin Anthony R., Vasseur Jean-Jacques, Smietana Michael: Boron and nucleic acid chemistries: merging the best of both worlds. Chem. Soc. Rev. 2013, 42, 5684. <http://dx.doi.org/10.1039/c3cs60038f>
  • Kuznetsov Nikolai Yu., Maleev Victor I., Khrustalev Victor N., Mkrtchyan Anna F., Godovikov Ivan A., Strelkova Tatyana V., Bubnov Yuri N.: A New Method of Synthesis of 6-Substituted Piperidine-2,4-diones from Homoallylamines. Eur J Org 2012, 2012, 334. <http://dx.doi.org/10.1002/ejoc.201101114>
  • Chen Jiawei, Venkatasubbaiah Krishnan, Pakkirisamy Thilagar, Doshi Ami, Yusupov Andrej, Patel Yesha, Lalancette Roger A., Jäkle Frieder: Planar Chiral Organoborane Lewis Acids Derived from Naphthylferrocene. Chem Eur J 2010, 16, 8861. <http://dx.doi.org/10.1002/chem.201000372>
  • González Ana Z., Román José G., Alicea Eyleen, Canales Eda, Soderquist John A.: Borabicyclo[3.3.2]decanes and the Stereoselective Asymmetric Synthesis of 1,3-Diol Stereotriads from 1,3-Diborylpropenes. J Am Chem Soc 2009, 131, 1269. <http://dx.doi.org/10.1021/ja808360z>
  • González Javier R., González Ana Z., Soderquist John A.: (E)-2-Boryl-1,3-butadiene Derivatives of the 10-TMS-9-BBDs: Highly Selective Reagents for the Asymmetric Synthesis of anti-1,2-Disubstituted 3,4-Pentadien-1-ols. J Am Chem Soc 2009, 131, 9924. <http://dx.doi.org/10.1021/ja9047202>
  • Canales Eda, Gonzalez Ana Z., Soderquist John A.: Asymmetric Synthesis of Isomerically Pure Allenyl Boranes from Alkynyl Boranes through a 1,2-Insertion–1,3-Borotropic Rearrangement. Angew Chem 2007, 119, 401. <http://dx.doi.org/10.1002/ange.200603467>
  • Canales Eda, Gonzalez Ana Z., Soderquist John A.: Asymmetric Synthesis of Isomerically Pure Allenyl Boranes from Alkynyl Boranes through a 1,2-Insertion–1,3-Borotropic Rearrangement. Angew Chem Int Ed 2007, 46, 397. <http://dx.doi.org/10.1002/anie.200603467>
  • Hernandez Eliud, Canales Eda, Gonzalez Eduvigis, Soderquist John A.: Asymmetric Synthesis with the Robust and Versatile 10-Substituted 9-Borabicyclo[3.3.2]decanes: Homoallylic Amines from Aldimines. ChemInform 2007, 38. <http://dx.doi.org/10.1002/chin.200701249>
  • Petasis Nicos A.: Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry. Aust J Chem 2007, 60, 795. <http://dx.doi.org/10.1071/CH07360>
  • Gonzalez Ana Z., Canales Eda, Soderquist John A.: N-Propargylamides via the Asymmetric Michael Addition of B-Alkynyl-10-TMS-9- borabicyclo[3.3.2]decanes to N-Acylimines. Org Lett 2006, 8, 3331. <http://dx.doi.org/10.1021/ol0611595>