Synthesis, resolution, and applications of 3-amino-2,2-dimethyl-1,3- diphenylpropan-1-ol, a conformationally restricted 1,3-aminoalcohol

  • Patil M
  • Gonnade R
  • Joshi N
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Abstract

Efficient synthetic routes to both syn and anti diastereomers of a conformationally restricted 1,3-aminoalcohol were devised. Resolution of the aminoalcohols was accomplished through diastereomeric salt with R-(-)-O-acetyl mandelic acid. These aminoalcohols were examined as ligands for two standard reactions, namely, enantioselective addition of Et2Zn to aldehydes and reduction of prochiral ketones with BH3. © 2010 Elsevier Ltd.

Author-supplied keywords

  • 1,3-Aminoalcohol
  • Aldol-Tishchenko reaction
  • Diethylzinc
  • Oxazaborinane
  • Resolution

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Authors

  • M. N. Patil

  • R. G. Gonnade

  • N. N. Joshi

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