Highly Active Chiral Phosphoramide−Zn(II) Complexes as Conjugate Acid−Base Catalysts for Enantioselective Organozinc Addition to Ketones

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Abstract

A highly efficient enantioselective organozinc (R₂Zn) addition to ketones catalyzed by chiral phosphoramide−Zn(II) complexes (1−10 mol %) has been developed. These complexes serve as conjugate Lewis acid−Lewis base catalysts. Chiral phosphoramides are derived from an inexpensive natural amino acid (i.e., l-valine). From a variety of nonactivated aromatic and aliphatic ketones, the corresponding optically active tertiary alcohols were obtained in high yields with high enantioselectivities (up to 98% ee) under the mild reaction conditions.

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This article has been cited by 7 ACS Journal articles (5 most recent appear below).

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    Monika I. Antczak, Feng Cai, and Joseph M. Ready
    Organic Letters2011 13 (2), 184-187

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

  Highly Enantioselective 3-Furylation of Ketones Using (3-Furyl)titanium Nucleophile

  Shuangliu Zhou, Chi-Ren Chen and Han-Mou Gau
  Organic Letters2010 12 (1), 48-51

  • Highly Enantioselective 3-Furylation of Ketones Using (3-Furyl)titanium Nucleophile

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    Organic Letters2010 12 (1), 48-51

    A novel asymmetric 3-furyl addition of (3-furyl)Ti(OiPr)3 to ketones in the presence of 10 mol % (S)-BINOL is reported. The catalytic system works excellently for aromatic ketones, α- or β-halophenones, α,β-unsaturated ketones, and acetylfuran, ...

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

  Direct Asymmetric Catalytic Thienylaluminum Addition to Ketones: A Concise Approach to the Synthesis of (S)-Tiemonium Iodide

  Deepak B. Biradar, Shuangliu Zhou and Han-Mou Gau
  Organic Letters2009 11 (15), 3386-3389

  • Direct Asymmetric Catalytic Thienylaluminum Addition to Ketones: A Concise Approach to the Synthesis of (S)-Tiemonium Iodide

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    Organic Letters2009 11 (15), 3386-3389

    A direct asymmetric addition of a (2-thienyl)aluminum reagent to ketones catalyzed by a titanium catalyst of (S)-BINOL to afford chiral tertiary 2-thienyl alcohols is reported. The catalytic system works excellently for aromatic ketones and for 1-...

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

  Highly Enantioselective Arylation of Aldehydes and Ketones Using AlArEt₂(THF) as Aryl Sources

  Shuangliu Zhou, Kuo-Hui Wu, Chien-An Chen and Han-Mou Gau
  The Journal of Organic Chemistry2009 74 (9), 3500-3505

  • Highly Enantioselective Arylation of Aldehydes and Ketones Using AlArEt₂(THF) as Aryl Sources

    Shuangliu Zhou, Kuo-Hui Wu, Chien-An Chen and Han-Mou Gau
    The Journal of Organic Chemistry2009 74 (9), 3500-3505

    A series of AlArEt2(THF) (Ar = Ph (1a), 4-MeC6H4 (1b), 4-MeOC6H4 (1c), 4-Me3SiC6H4 (1d), 2-naphthyl (1e)) were synthesized from reactions of AlEt2Br(THF) with ArMgBr. In CDCl3 solution, the 1H NMR spectra showed that AlArEt2(THF) compounds exist as a ...

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

  N to C Aryl Migration in Lithiated Carbamates: α-Arylation of Benzylic Alcohols

  Jonathan Clayden, William Farnaby, Damian M. Grainger, Ulrich Hennecke, Michele Mancinelli, Daniel J. Tetlow, Ian H. Hillier and Mark A. Vincent
  Journal of the American Chemical Society2009 131 (10), 3410-3411

  • N to C Aryl Migration in Lithiated Carbamates: α-Arylation of Benzylic Alcohols

    Jonathan Clayden, William Farnaby, Damian M. Grainger, Ulrich Hennecke, Michele Mancinelli, Daniel J. Tetlow, Ian H. Hillier and Mark A. Vincent
    Journal of the American Chemical Society2009 131 (10), 3410-3411

    We report a new mode of reactivity displayed by lithiated O-benzyl carbamates carrying an N-aryl substituent: upon lithiation, the N-aryl group is transferred cleanly from N to C. An arylation of the carbamate results, providing a route to α,α-arylated ...

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

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