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Synthesis 1989; 1989(9): 703-706
DOI: 10.1055/s-1989-27367
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Tributyltin Cyanide, a Novel Reagent for the Stereoselective Preparation of 3-Amino-2-hydroxy Acids via Cyanohydrin Intermediates

Rosario Herranz* , Julia Castro-Pichel, Teresa García-López
  • *Instituto de Química Médica (CSIC), Juan de la Cierva, 3. 28006 Madrid, Spain
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Publication Date:
17 September 2002 (online)

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Reaction of tributyltin cyanide with optically active 2-N-benzyloxyearbonylamino aldehydes 1 gives the corresponding O-tributylstannyl cyanohydrins 2 and 3 stereoselectively. Compounds 2 and 3 are transformed in situ into the methyl 3-N-benzoyloxycarbonyl-amino-2-hydroxy esters 4 and 5, respectively, via the imidate hydrochloride intermediates. Saponification of 4 and 5 provide 3-amino-2-hydroxy acids 6 and 7, respectively, key intermediates in the preparation of Bestatin, Amastatin, and analogues.