Reversal of enantioselectivity by adding Ti(OiPr)4: Novel sulfamide-amine alcohol ligands for the catalytic asymmetric addition of diethylzinc to aldehydes

  • Mao J
  • Wan B
  • Zhang Z
 et al. 
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Abstract

Novel sulfamide-amine alcohols (6) were applied to the catalytic asymmetric addition of diethylzinc to aldehydes, providing (S)-products in high yields and good enantioselectivities. These sulfamide-amie alcohols together with Ti(OiPr)4were shown to obtain the (R)-products in significant enantiomeric excesses and high yields. Novel sulfamide-amine alcohol ligands (6) derived from (-)-ephedrine (4a) and (+)-pseudoephedrine (4b) with multiple stereogenic centers were applied to the catalytic asymmetric addition of diethylzinc to aldehydes, providing (S)-products in high yields and good enantioselectivities. These sulfamide-amine alcohols together with Ti(OiPr)4were shown to obtain the (R)-products in significant enantiomeric excesses (e.e.) and high yields. In addition, sulfamide-amine alcohols were superior to the original chiral sources 4a and 4b, which afforded no enantioselectivity in the Ti(OiPr)4-mediated reaction. © 2004 Elsevier B.V. All rights reserved.

Author-supplied keywords

  • Aldehyde
  • Catalytic asymmetric addition
  • Diethylzinc
  • Reversal of enantioselectivity
  • Sulfamide-amine alcohol

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Authors

  • Jincheng Mao

  • Boshun Wan

  • Zhanjin Zhang

  • Rongliang Wang

  • Fan Wu

  • Shiwei Lu

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