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Pure Appl. Chem., 2006, Vol. 78, No. 7, pp. 1397-1406

http://dx.doi.org/10.1351/pac200678071397

Recent developments in the chiral synthesis of homoallylic amines via organoboranes

P. Veeraraghavan Ramachandran and Thomas E. Burghardt

Herbert C. Brown Center for Borane Research, Department of Chemistry,Purdue University, 560 Oval Dr., West Lafayette, IN 47907-2084, USA

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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>
  • Cui Yi, Li Wei, Sato Takehiro, Yamashita Yasuhiro, Kobayashi Shū: Catalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones. Adv. Synth. Catal. 2013, 355, 1193. <http://dx.doi.org/10.1002/adsc.201201134>
  • Gandhi Shikha, List Benjamin: Catalytic Asymmetric Three-Component Synthesis of Homoallylic Amines. Angew. Chem. 2013, 125, 2633. <http://dx.doi.org/10.1002/ange.201209776>
  • Gandhi Shikha, List Benjamin: Catalytic Asymmetric Three-Component Synthesis of Homoallylic Amines. Angew. Chem. Int. Ed. 2013, 52, 2573. <http://dx.doi.org/10.1002/anie.201209776>
  • Kobayashi Shū, Endo Toshimitsu, Yoshino Takumi, Schneider Uwe, Ueno Masaharu: Allylation Reactions of Aldehydes with Allylboronates in Aqueous Media: Unique Reactivity and Selectivity that are Only Observed in the Presence of Water. Chem. Asian J. 2013, 8, 2033. <http://dx.doi.org/10.1002/asia.201300440>
  • Lei Qian, Wei Yawen, Talwar Dinesh, Wang Chao, Xue Dong, Xiao Jianliang: Fast Reductive Amination by Transfer Hydrogenation “on Water”. Chem. Eur. J. 2013, 19, 4021. <http://dx.doi.org/10.1002/chem.201204194>
  • 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>
  • Lee Jin Hee, Gupta Sreya, Jeong Wook, Rhee Young Ho, Park Jaiwook: Characterization and Utility of N-Unsubstituted Imines Synthesized from Alkyl Azides by Ruthenium Catalysis. Angew. Chem. 2012, 124, 11009. <http://dx.doi.org/10.1002/ange.201204483>
  • Lee Jin Hee, Gupta Sreya, Jeong Wook, Rhee Young Ho, Park Jaiwook: Characterization and Utility of N-Unsubstituted Imines Synthesized from Alkyl Azides by Ruthenium Catalysis. Angew. Chem. Int. Ed. 2012, 51, 10851. <http://dx.doi.org/10.1002/anie.201204483>
  • Nugent Thomas C., El-Shazly Mohamed: Chiral Amine Synthesis - Recent Developments and Trends for Enamide Reduction, Reductive Amination, and Imine Reduction. Synth Catal 2010, 352, 753. <http://dx.doi.org/10.1002/adsc.200900719>
  • Ros Abel, Bermejo Antonio, Aggarwal Varinder K.: Benzylic Boron Reagents Behaving as Allylic Boron Reagents towards Aldehydes: A New Asymmetric Reaction Leading to Homoallylic Alcohols with Concomitant Dearomatisation. Chem Eur J 2010, 16, 9741. <http://dx.doi.org/10.1002/chem.201001174>
  • Zhang Xiaowen, Qiu Renhua, Tan Nianyuan, Yin Shuangfeng, Xia Jun, Luo Shenglian, Au Chak-Tong: Air-stable hypervalent organobismuth(III) tetrafluoroborate as effective and reusable catalyst for the allylation of aldehyde with tetraallyltin. Tetrahetron Lett 2010, 51, 153. <http://dx.doi.org/10.1016/j.tetlet.2009.10.104>
  • Yus Miguel, Foubelo Francisco, K. Dema Haythem: Stereoselective Synthesis of α-Methylene-γ-butyrolactams from Ethyl 2-(Bromomethyl)acrylate and Chiral Sulfinyl Aldimines Mediated by Indium. HETEROCYLES 2010, 80, 125. <http://dx.doi.org/10.3987/COM-09-S(S)27>
  • Takahashi Masayuki, McLaughlin Martin, Micalizio Glenn C.: Complex Allylation by the Direct Cross-Coupling of Imines with Unactivated Allylic Alcohols. Angew Chem 2009, 121, 3702. <http://dx.doi.org/10.1002/ange.200900236>
  • Takahashi Masayuki, McLaughlin Martin, Micalizio Glenn C.: Complex Allylation by the Direct Cross-Coupling of Imines with Unactivated Allylic Alcohols. Angew Chem Int Ed 2009, 48, 3648. <http://dx.doi.org/10.1002/anie.200900236>
  • YUE Xuyi, QIU Xiaolong, QING Fengling: Metal-mediated gem-Difluoroallylation of N-Acylhydrazones: Highly Efficient Synthesis of α,α-Difluorohomoallylic Amines. Chin J Chem 2009, 27, 141. <http://dx.doi.org/10.1002/cjoc.200990007>
  • Pietruszka J��rg, Solduga Gemma: Enantiomerically Pure Cyclopropylamines from Cyclopropylboronic Esters. Eur J Org Chem 2009, 2009, 5998. <http://dx.doi.org/10.1002/ejoc.200900882>
  • Kobayashi Shū, Konishi Hideyuki, Schneider Uwe: Indium(i) iodide-catalyzed regio- and diastereoselective formal α-addition of an α-methylallylboronate to N-acylhydrazones. Chem Commun 2008, 2313. <http://dx.doi.org/10.1039/b802153h>
  • Esquivias Jorge, Gómez Arrayás Ramón, Carretero Juan Carlos: Alkylation of ArylN-(2-Pyridylsulfonyl)aldimines with Organozinc Halides: Conciliation of Reactivity and Chemoselectivity. Angew Chem 2007, 119, 9417. <http://dx.doi.org/10.1002/ange.200703239>
  • Esquivias Jorge, Gómez Arrayás Ramón, Carretero Juan Carlos: Alkylation of ArylN-(2-Pyridylsulfonyl)aldimines with Organozinc Halides: Conciliation of Reactivity and Chemoselectivity. Angew Chem Int Ed 2007, 46, 9257. <http://dx.doi.org/10.1002/anie.200703239>
  • Ramachandran P. Veeraraghavan, Burghardt Thomas E.: Recent Developments in the Chiral Synthesis of Homoallylic Amines via Organoboranes. ChemInform 2007, 38. <http://dx.doi.org/10.1002/chin.200702260>
  • Valpuesta María, Muñoz Carmen, Díaz Amelia, Suau Rafael, Torres Gregorio: Organoborane Reagents in theC-Alkylation of Aromatic Aldimines. Eur J Org Chem 2007, 2007, 4467. <http://dx.doi.org/10.1002/ejoc.200700400>
  • Friestad Gregory K., Mathies Alex K.: Recent developments in asymmetric catalytic addition to CN bonds. Tetrahedron 2007, 63, 2541. <http://dx.doi.org/10.1016/j.tet.2006.11.076>
  • Zhou Yan, Shan Zixing: Novel Grignard reaction of chelated boric esters derived from diethyl (2R,3R)-tartrate: a one-step access to a bulky γ,γ,γ-trisubstituted γ-hydroxy-β-ketoester via selective arylation and sequent deboronation. Tetrahetron Lett 2007, 48, 3531. <http://dx.doi.org/10.1016/j.tetlet.2007.03.098>
  • 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>