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Pure Appl. Chem., 1998, Vol. 70, No. 5, pp. 1117-1122

http://dx.doi.org/10.1351/pac199870051117

Metal-catalyzed asymmetric hetero-DielsAlder reactions of unactivated dienes with glyoxylates

Mogens Johannsen, Sulan Yao, Anette Graven and K. A. Jørgensen

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  • Umamaheswari V., Cias Pawel, Pöppl Andreas, Kaupp Martin, Gescheidt Georg: Ligand spheres in asymmetric hetero Diels–Alder reactions catalyzed by Cu(ii) box complexes: experiment and modeling. Dalton Trans. 2014, 43, 698. <http://dx.doi.org/10.1039/c3dt51602d>
  • Tan Jiajing, Cheon Cheol-Hong, Yamamoto Hisashi: Catalytic Asymmetric Claisen Rearrangement of Enolphosphonates: Construction of Vicinal Tertiary and All-Carbon Quaternary Centers. Angew. Chem. 2012, 124, 8389. <http://dx.doi.org/10.1002/ange.201203092>
  • Tan Jiajing, Cheon Cheol-Hong, Yamamoto Hisashi: Catalytic Asymmetric Claisen Rearrangement of Enolphosphonates: Construction of Vicinal Tertiary and All-Carbon Quaternary Centers. Angew. Chem. Int. Ed. 2012, 51, 8264. <http://dx.doi.org/10.1002/anie.201203092>
  • Carmona Daniel, Viguri Fernando, Asenjo Ainara, Lamata M. Pilar, Lahoz Fernando, Garcı́a-Orduña Pilar, Oro L. A.: Enantioselective Catalysts for the Diels–Alder Reaction between Methacrolein and Cyclopentadiene Based on the Chiral Fragment (η5-C5Me5)M(chiral diphosphane) (M = Rh, Ir). Organomettalics 2011, 30, 6661. <http://dx.doi.org/10.1021/om200859z>
  • JOHANNSEN M., YAO S., GRAVEN A., JORGENSEN K. A.: ChemInform Abstract: Metal-Catalyzed Asymmetric hetero-Diels-Alder Reactions of Unactivated Dienes with Glyoxylates. ChemInform 2010, 29, no. <http://dx.doi.org/10.1002/chin.199851321>
  • Endeshaw Molla Mellese, Bayer Annette, Hansen Lars K., Gautun Odd R.: Catalytic Asymmetric Hetero Diels–Alder Reactions ofN-Sulfinyl Dienophiles with Chiral Bis(oxazoline)copper(II) and -zinc(II) Triflates. Eur J Org Chem 2006, 2006, 5249. <http://dx.doi.org/10.1002/ejoc.200600083>
  • Berkessel Albrecht, Vogl Nadine: DIANANE-CrIII-salen Complexes as Highly Enantioselective Catalysts for Hetero-Diels–Alder Reactions of Aldehydes with Dienes. Eur J Org Chem 2006, 2006, 5029. <http://dx.doi.org/10.1002/ejoc.200600359>
  • Verma Shyam S., Dwivedi Namrata, Singh Biswajit K., Tripathi Rama P.: DBU assisted expeditious synthesis of glycosyl dienes via glycosylated β-hydroxy esters. Carbohydrates Research 2006, 341, 1930. <http://dx.doi.org/10.1016/j.carres.2006.04.021>
  • Bolm Carsten, Verrucci Marinella, Simic Oliver, Hackenberger Christian P. R.: Ethylene-Bridged Bissulfoximines in Copper-Catalyzed Enantioselective Hetero-Diels--Alder Reactions. Adv Synth Catal 2005, 347, 1696. <http://dx.doi.org/10.1002/adsc.200505104>
  • Burgess Kerrie L., Corbett Matthew S., Eugenio Paul, Lajkiewicz Neil J., Liu Xiang, Sanyal Amitav, Yan Wanlin, Yuan Qian, Snyder John K.: Chiral anthracene and anthrone templates as stereocontrolling elements in Diels–Alder/retro Diels–Alder sequences. biorg med chem 2005, 13, 5299. <http://dx.doi.org/10.1016/j.bmc.2005.06.025>
  • Kwiatkowski Piotr, Chaładaj Wojciech, Malinowska Małgorzata, Asztemborska Monika, Jurczak Janusz: The high-pressure [4+2]cycloaddition of 1-methoxybuta-1,3-diene to the glycolaldehyde-derived heterodienophiles, catalyzed by chiral metallosalen complexes. Tet Asymm 2005, 16, 2959. <http://dx.doi.org/10.1016/j.tetasy.2005.07.031>
  • Dalko Peter I., Moisan Lionel, Cossy Janine: Modular Ligands for Asymmetric Synthesis: Enantioselective Catalytic CuII-Mediated Condensation Reaction of Ethyl Pyruvate with Danishefsky's Diene. Angew Chem 2002, 114, 647. <http://dx.doi.org/10.1002/1521-3757(20020215)114:4<647::AID-ANGE647>3.0.CO;2-Z>
  • Dalko Peter I., Moisan Lionel, Cossy Janine: Modular Ligands for Asymmetric Synthesis: Enantioselective Catalytic CuII-Mediated Condensation Reaction of Ethyl Pyruvate with Danishefsky's Diene. Angew Chem Int Ed 2002, 41, 625. <http://dx.doi.org/10.1002/1521-3773(20020215)41:4<625::AID-ANIE625>3.0.CO;2-U>
  • Pastor Isidro M, Adolfsson Hans: Novel highly modular C2-symmetric oxazoline ligands—application in titanium-catalyzed diethylzinc additions to aldehydes. Tetrahetron Lett 2002, 43, 1743. <http://dx.doi.org/10.1016/S0040-4039(02)00087-4>
  • Bayer Annette, Gautun Odd R.: Highly enantioselective hetero Diels–Alder reactions of N-sulfinyl dienophiles promoted by copper(II)- and zinc(II)-chiral bis(oxazoline) complexes. Tet Asymm 2001, 12, 2937. <http://dx.doi.org/10.1016/S0957-4166(01)00525-0>
  • Evans David A., Johnson Jeffrey S., Burgey Christopher S., Campos Kevin R.: Reversal in enantioselectivity of tert-butyl versus phenyl-substituted bis(oxazoline) copper(II) catalyzed hetero Diels-Alder and ene reactions. Crystallographic and mechanistic studies. Tetrahetron Lett 1999, 40, 2879. <http://dx.doi.org/10.1016/S0040-4039(99)00395-0>