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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 409-414

http://dx.doi.org/10.1351/pac200678020409

Dual Lewis acid - Lewis base activation in enantioselective additions to aldehydes

Erica Wingstrand, Stina Lundgren, Maël Penhoat and Christina Moberg

Department of Chemistry, Organic Chemistry, Royal Institute of Technology, SE 100 44 Stockholm, Sweden

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  • Wen Ye-Qian, Hertzberg Robin, Gonzalez Inanllely, Moberg Christina: Minor Enantiomer Recycling: Application to Enantioselective Syntheses of Beta Blockers. Chem. Eur. J. 2014, 20, 3806. <http://dx.doi.org/10.1002/chem.201303890>
  • Wang Sa, Bromberg Lev, Schreuder-Gibson Heidi, Hatton T. Alan: Organophophorous Ester Degradation by Chromium(III) Terephthalate Metal–Organic Framework (MIL-101) Chelated to N,N-Dimethylaminopyridine and Related Aminopyridines. ACS Appl. Mater. Interfaces 2013, 5, 1269. <http://dx.doi.org/10.1021/am302359b>
  • Hertzberg Robin, Moberg Christina: One-Step Preparation of O-(α-Bromoacyl) Cyanohydrins by Minor Enantiomer Recycling: Synthesis of 4-Amino-2(5H)-furanones. J. Org. Chem. 2013, 78, 9174. <http://dx.doi.org/10.1021/jo401401c>
  • Hertzberg Robin, Widyan Khalid, Heid Berenice, Moberg Christina: Enantioenriched ω-bromocyanohydrin derivatives. Improved selectivity by combination of two chiral catalysts. Tetrahedron 2012, 68, 7680. <http://dx.doi.org/10.1016/j.tet.2012.05.090>
  • Stegbauer Linus, Sladojevich Filippo, Dixon Darren J.: Bifunctional organo/metal cooperative catalysis with cinchona alkaloid scaffolds. Chem Sci 2012, 3, 942. <http://dx.doi.org/10.1039/c1sc00416f>
  • Kodama Koichi, Kawamata Hiroaki, Takahashi Naoya, Hirose Takuji: Cyanative self-condensation of aromatic aldehydes promoted by VO(OiPr)3–Lewis base as a cooperative catalyst. Org. Biomol. Chem. 2012, 10, 9440. <http://dx.doi.org/10.1039/c2ob26811f>
  • Laurell Anna, Moberg Christina: Opposite Enantiomers from Minor Enantiomer Recycling and Dynamic Kinetic Resolution Using a Single Biocatalyst. Eur J Org Chem 2011, 2011, 3980. <http://dx.doi.org/10.1002/ejoc.201100467>
  • Zhang Zhipeng, Wang Zheng, Zhang Ruzhou, Ding Kuiling: An Efficient Titanium Catalyst for Enantioselective Cyanation of Aldehydes: Cooperative Catalysis. Angew Chem 2010, 122, 6898. <http://dx.doi.org/10.1002/ange.201002127>
  • North Michael: Ein zweikerniger Titankatalysator zur enantioselektiven Cyanierung von Aldehyden durch kooperative Katalyse. Angew Chem 2010, 122, 8255. <http://dx.doi.org/10.1002/ange.201003014>
  • Zhang Zhipeng, Wang Zheng, Zhang Ruzhou, Ding Kuiling: An Efficient Titanium Catalyst for Enantioselective Cyanation of Aldehydes: Cooperative Catalysis. Angew Chem Int Ed 2010, 49, 6746. <http://dx.doi.org/10.1002/anie.201002127>
  • North Michael: A Bimetallic Titanium Catalyst for the Enantioselective Cyanation of Aldehydes Based on Cooperative Catalysis. Angew Chem Int Ed 2010, 49, 8079. <http://dx.doi.org/10.1002/anie.201003014>
  • Belokon Yuri N., Clegg William, Harrington Ross W., Maleev Victor I., North Michael, Pujol Marta Omedes, Usanov Dmitry L., Young Carl: Mechanism-Guided Development of VO(salen)X Complexes as Catalysts for the Asymmetric Synthesis of Cyanohydrin Trimethylsilyl Ethers. Chem Eur J 2009, 15, 2148. <http://dx.doi.org/10.1002/chem.200801679>
  • Li Fei, Widyan Khalid, Wingstrand Erica, Moberg Christina: Chiral Lewis Base Catalyzed Enantioselective Acetylcyanation of α-Oxo Esters. Eur J Org Chem 2009, 2009, 3917. <http://dx.doi.org/10.1002/ejoc.200900055>
  • Lundgren Stina, Wingstrand Erica, Moberg Christina: Lewis Acid–Lewis Base-Catalysed Enantioselective Addition of α-Ketonitriles to Aldehydes. Adv Synth Catal 2007, 349, 364. <http://dx.doi.org/10.1002/adsc.200600365>
  • Hamberg Anders, Lundgren Stina, Wingstrand Erica, Moberg Christina, Hult Karl: High-Throughput Synthesis and Analysis of Acylated Cyanohydrins. Chem Eur J 2007, 13, 4334. <http://dx.doi.org/10.1002/chem.200601638>
  • Belokon Yuri N., Clegg William, Harrington Ross W., Young Carl, North Michael: Asymmetric cyanohydrin synthesis using heterobimetallic catalysts obtained from titanium and vanadium complexes of chiral and achiral salen ligands. Tetrahedron 2007, 63, 5287. <http://dx.doi.org/10.1016/j.tet.2007.03.140>
  • Belokon' Yuri N., Clegg William, Harrington Ross W., Ishibashi Eisuke, Nomura Hiroshi, North Michael: Enantioselective and diastereoselective syntheses of cyanohydrin carbonates. Tetrahedron 2007, 63, 9724. <http://dx.doi.org/10.1016/j.tet.2007.07.016>
  • Wingstrand Erica, Lundgren Stina, Penhoat Mael, Moberg Christina: Dual Lewis Acid—Lewis Base Activation in Enantioselective Additions to Aldehydes. ChemInform 2006, 37. <http://dx.doi.org/10.1002/chin.200631247>