3,3‘-Br₂-BINOL-Zn Complex:  A Highly Efficient Catalyst for the Enantioselective Hetero-Diels−Alder Reaction

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Abstract

A BINOLate-zinc complex prepared in situ from Et₂Zn and 3,3‘-dibromo-1,1‘-bi-2-naphthol (3,3‘-Br₂-BINOL) was found to be a highly efficient catalyst for the enantioselective hetero-Diels−Alder reaction of Danishefsky's diene and aldehydes to give 2-substituted 2,3-dihydro-4H-pyran-4-one in up to quantitative yield and 98% ee.

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This article has been cited by 15 ACS Journal articles (5 most recent appear below).

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  Asymmetric Synthesis of 2,3-Dihydro-4-pyranones by Reaction of Chiral 3-Alkoxycyclobutanone and Aldehydes

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  • Asymmetric Synthesis of 2,3-Dihydro-4-pyranones by Reaction of Chiral 3-Alkoxycyclobutanone and Aldehydes

    Shoko Negishi, Hiroyuki Ishibashi, and Jun-ichi Matsuo
    Organic Letters2010 12 (21), 4984-4987

    Chiral cyclobutanone which had ethyl l-lactate as a chiral auxiliary at the 3-position reacted with aldehydes to give 2,3-dihydro-4-pyranones in up to 93% ee by combined use of titanium(IV) chloride and tin(II) chloride.

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Resolution of Planar-Chiral Ferrocenylborane Lewis Acids: The Impact of Steric Effects on the Stereoselective Binding of Ephedrine Derivatives

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  • Resolution of Planar-Chiral Ferrocenylborane Lewis Acids: The Impact of Steric Effects on the Stereoselective Binding of Ephedrine Derivatives

    Ramez Boshra, Krishnan Venkatasubbaiah, Ami Doshi and Frieder Jäkle
    Organometallics2009 28 (14), 4141-4149

    Resolution of the planar-chiral bidentate Lewis acid Fc[B(Cl)Me][SnMe2Cl] (Fc = 1,2-ferrocenediyl) (1) by complexation with pseudoephedrine derivatives was studied. Compound 1 was first converted to the methoxy derivative Fc[B(OMe)Me][SnMe2Cl] (2) by ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Highly Enantioselective Hetero- Diels−Alder Reaction of trans-1-Methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with Aromatic and Aliphatic Aldehydes Catalyzed by 3-Substituted BINOL−Titanium Complex

  Xin-Bin Yang, Jie Feng, Ji Zhang, Na Wang, Li Wang, Jun-Liang Liu, and Xiao-Qi Yu
  Organic Letters2008 10 (6), 1299-1302

  • Highly Enantioselective Hetero- Diels−Alder Reaction of trans-1-Methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with Aromatic and Aliphatic Aldehydes Catalyzed by 3-Substituted BINOL−Titanium Complex

    Xin-Bin Yang, Jie Feng, Ji Zhang, Na Wang, Li Wang, Jun-Liang Liu, and Xiao-Qi Yu
    Organic Letters2008 10 (6), 1299-1302

    3-Diphenylhydroxymethyl-substituted BINOLtitanium complex prepared in situ was found to be a highly efficient catalyst for hetero-DielsAlder reaction of diene 1 with both aromatic and aliphatic aldehydes to give 2,5-disubstituted dihydropyrone in up to ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  A Green Chemistry Approach to Asymmetric Catalysis:  Solvent-Free and Highly Concentrated Reactions

  Patrick J. Walsh, Hongmei Li, and Cecilia Anaya de Parrodi
  Chemical Reviews2007 107 (6), 2503-2545

  • A Green Chemistry Approach to Asymmetric Catalysis:  Solvent-Free and Highly Concentrated Reactions

    Patrick J. Walsh, Hongmei Li, and Cecilia Anaya de Parrodi
    Chemical Reviews2007 107 (6), 2503-2545
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Highly Enantio- and Diastereoselective Brassard Type Hetero-Diels−Alder Approach to 5-Methyl-Containing α,β-Unsaturated δ-Lactones

  Lili Lin, Qian Fan, Bo Qin, and Xiaoming Feng
  The Journal of Organic Chemistry2006 71 (11), 4141-4146

  • Highly Enantio- and Diastereoselective Brassard Type Hetero-Diels−Alder Approach to 5-Methyl-Containing α,β-Unsaturated δ-Lactones

    Lili Lin, Qian Fan, Bo Qin, and Xiaoming Feng
    The Journal of Organic Chemistry2006 71 (11), 4141-4146

    Two efficient new chiral copper (II) Schiff base complexes were developed for the highly enantio- and diastereoselective HDA reaction of Brassard type diene 1b with aldehydes, to afford the corresponding 5-methyl-containing α,β-unsaturated δ-lactone ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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