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Synthesis 1990; 1990(9): 779-781
DOI: 10.1055/s-1990-27012
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Stereospecific Synthesis of N-(Diphenylmethylene)-α,β-didehydroamino Acid Methyl Esters from β-Hydroxy-α-amino Acids

Cesarino Balsamini* , Ermanno Duranti, Leonardo Mariani, Americo Salvatori, Gilberto Spadoni
  • *Istituto di Chimica Farmaceutica, Università di Urbino, Piazza del Rinascimento 6, I-61029 Urbino, Italy
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Publication Date:
17 September 2002 (online)

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N-(Diphenylmethylene)-α,β-didehydroamino acid methyl esters 2b-d are prepared with absolute geometric selectivity from inexpensive β-hydroxyamino acids through the intermediates N-(diphenylmethylene)- β-hydroxyamino acid methyl esters 1b-d. Besides, an easy conversion from E isomers to the corresponding Z isomers was performed, thus avoiding the use of the uncommon allo-β-hydroxyamino acids as starting materials.