Organocatalysis

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Editor: Prof. Benjamin List
Max-Planck-Institut für Kohlenforschung
 
Organocatalysis describes catalysis with low-molecular-weight organic compounds, in which a metal is not part of the active principle. Organocatalysts donate or remove electrons or protons as their activation mode. There are additional aspects that belong to the field and that are being actively researched, including supported catalysts, organocatalysis in unusual reaction media, and applications in polymerizations, in total synthesis and drug-discovery, as well as in drug manufacturing, among many others. Certain things that cannot be done with enzymes or metals may well be feasible with organic catalysts.

See also the Thematic Series:
Transition-metal and organocatalysis in natural product synthesis
Sustainable catalysis

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Organocatalysis

  • Benjamin List

Beilstein J. Org. Chem. 2012, 8, 1358–1359, doi:10.3762/bjoc.8.156

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Editorial
Published 23 Aug 2012

Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles

  • Pavol Jakubec,
  • Dane M. Cockfield,
  • Madeleine Helliwell,
  • James Raftery and
  • Darren J. Dixon

Beilstein J. Org. Chem. 2012, 8, 567–578, doi:10.3762/bjoc.8.64

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Published 16 Apr 2012

Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition

  • Kazato Inanaga,
  • Yu Ogawa,
  • Yuuki Nagamoto,
  • Akihiro Daigaku,
  • Hidetoshi Tokuyama,
  • Yoshiji Takemoto and
  • Kiyosei Takasu

Beilstein J. Org. Chem. 2012, 8, 658–661, doi:10.3762/bjoc.8.73

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Published 27 Apr 2012

Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts

  • Saet Byeol Woo and
  • Dae Young Kim

Beilstein J. Org. Chem. 2012, 8, 699–704, doi:10.3762/bjoc.8.78

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Published 07 May 2012

Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides

  • Hong-Ping Deng,
  • De Wang,
  • Yin Wei and
  • Min Shi

Beilstein J. Org. Chem. 2012, 8, 1098–1104, doi:10.3762/bjoc.8.121

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Published 16 Jul 2012

Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

  • Dieter Enders,
  • Jeanne Fronert,
  • Tom Bisschops and
  • Florian Boeck

Beilstein J. Org. Chem. 2012, 8, 1112–1117, doi:10.3762/bjoc.8.123

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Published 18 Jul 2012

Combined bead polymerization and Cinchona organocatalyst immobilization by thiol–ene addition

  • Kim A. Fredriksen,
  • Tor E. Kristensen and
  • Tore Hansen

Beilstein J. Org. Chem. 2012, 8, 1126–1133, doi:10.3762/bjoc.8.125

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Published 20 Jul 2012

Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters

  • Wen-Bin Yi,
  • Xin Huang,
  • Zijuan Zhang,
  • Dian-Rong Zhu,
  • Chun Cai and
  • Wei Zhang

Beilstein J. Org. Chem. 2012, 8, 1233–1240, doi:10.3762/bjoc.8.138

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Published 03 Aug 2012

Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins

  • Hang Zhang,
  • Shan-Jun Zhang,
  • Qing-Qing Zhou,
  • Lin Dong and
  • Ying-Chun Chen

Beilstein J. Org. Chem. 2012, 8, 1241–1245, doi:10.3762/bjoc.8.139

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Published 06 Aug 2012

Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones

  • Chunhui Jiang,
  • Fangrui Zhong and
  • Yixin Lu

Beilstein J. Org. Chem. 2012, 8, 1279–1283, doi:10.3762/bjoc.8.144

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Published 13 Aug 2012

Asymmetric one-pot sequential Friedel–Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme

  • Kengo Akagawa,
  • Ryota Umezawa and
  • Kazuaki Kudo

Beilstein J. Org. Chem. 2012, 8, 1333–1337, doi:10.3762/bjoc.8.152

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Published 17 Aug 2012

Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

  • Jin-Sheng Yu,
  • Feng Zhou,
  • Yun-Lin Liu and
  • Jian Zhou

Beilstein J. Org. Chem. 2012, 8, 1360–1365, doi:10.3762/bjoc.8.157

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Published 23 Aug 2012

Organocatalytic C–H activation reactions

  • Subhas Chandra Pan

Beilstein J. Org. Chem. 2012, 8, 1374–1384, doi:10.3762/bjoc.8.159

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Published 27 Aug 2012

Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels–Alder reactions

  • Stefan Bräse,
  • Nicole Volz,
  • Franziska Gläser and
  • Martin Nieger

Beilstein J. Org. Chem. 2012, 8, 1385–1392, doi:10.3762/bjoc.8.160

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Published 28 Aug 2012

Cation affinity numbers of Lewis bases

  • Christoph Lindner,
  • Raman Tandon,
  • Boris Maryasin,
  • Evgeny Larionov and
  • Hendrik Zipse

Beilstein J. Org. Chem. 2012, 8, 1406–1442, doi:10.3762/bjoc.8.163

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Published 31 Aug 2012

Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis

  • Marcus Frings,
  • Isabelle Thomé and
  • Carsten Bolm

Beilstein J. Org. Chem. 2012, 8, 1443–1451, doi:10.3762/bjoc.8.164

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Published 03 Sep 2012

Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones

  • Sergei Žari,
  • Tiiu Kailas,
  • Marina Kudrjashova,
  • Mario Öeren,
  • Ivar Järving,
  • Toomas Tamm,
  • Margus Lopp and
  • Tõnis Kanger

Beilstein J. Org. Chem. 2012, 8, 1452–1457, doi:10.3762/bjoc.8.165

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Published 04 Sep 2012

A quantitative approach to nucleophilic organocatalysis

  • Herbert Mayr,
  • Sami Lakhdar,
  • Biplab Maji and
  • Armin R. Ofial

Beilstein J. Org. Chem. 2012, 8, 1458–1478, doi:10.3762/bjoc.8.166

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Published 05 Sep 2012

Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity

  • Tatyana E. Shubina,
  • Matthias Freund,
  • Sebastian Schenker,
  • Timothy Clark and
  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2012, 8, 1485–1498, doi:10.3762/bjoc.8.168

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Published 07 Sep 2012

N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters

  • Takuya Uno,
  • Yusuke Kobayashi and
  • Yoshiji Takemoto

Beilstein J. Org. Chem. 2012, 8, 1499–1504, doi:10.3762/bjoc.8.169

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Published 10 Sep 2012

Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach

  • Florian Boeck,
  • Max Blazejak,
  • Markus R. Anneser and
  • Lukas Hintermann

Beilstein J. Org. Chem. 2012, 8, 1630–1636, doi:10.3762/bjoc.8.186

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Published 26 Sep 2012

Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives

  • Zhi-Cong Geng,
  • Jian Chen,
  • Ning Li,
  • Xiao-Fei Huang,
  • Yong Zhang,
  • Ya-Wen Zhang and
  • Xing-Wang Wang

Beilstein J. Org. Chem. 2012, 8, 1710–1720, doi:10.3762/bjoc.8.195

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Published 09 Oct 2012

Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines

  • Alan Armstrong and
  • Alexandra Ferguson

Beilstein J. Org. Chem. 2012, 8, 1747–1752, doi:10.3762/bjoc.8.199

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Published 12 Oct 2012

Asymmetric desymmetrization of meso-diols by C2-symmetric chiral 4-pyrrolidinopyridines

  • Hartmut Schedel,
  • Keizo Kan,
  • Yoshihiro Ueda,
  • Kenji Mishiro,
  • Keisuke Yoshida,
  • Takumi Furuta and
  • Takeo Kawabata

Beilstein J. Org. Chem. 2012, 8, 1778–1787, doi:10.3762/bjoc.8.203

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Published 17 Oct 2012

Imidazolinium and amidinium salts as Lewis acid organocatalysts

  • Oksana Sereda,
  • Nicole Clemens,
  • Tatjana Heckel and
  • René Wilhelm

Beilstein J. Org. Chem. 2012, 8, 1798–1803, doi:10.3762/bjoc.8.205

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Published 18 Oct 2012

Asymmetric Brønsted acid-catalyzed aza-Diels–Alder reaction of cyclic C-acylimines with cyclopentadiene

  • Magnus Rueping and
  • Sadiya Raja

Beilstein J. Org. Chem. 2012, 8, 1819–1824, doi:10.3762/bjoc.8.208

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Published 23 Oct 2012

Mechanochemistry assisted asymmetric organocatalysis: A sustainable approach

  • Pankaj Chauhan and
  • Swapandeep Singh Chimni

Beilstein J. Org. Chem. 2012, 8, 2132–2141, doi:10.3762/bjoc.8.240

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Published 06 Dec 2012
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