Tetrahedron p. 12337 - 12350 (1995)
Update date:2022-09-26
Topics:
Caputo, Romualdo
Cassano, Ersilia
Longobardo, Luigi
Palumbo, Giovanni
Enantiopure N-and/or C-protected homo-β-amino acids are prepared readily and in good yields from N-protected α-amino acids with the same side chain, via reduction of the carboxyl function and conversion of the resulting N-protected β-amino alcohol into the corresponding β-amino iodide and then β-amino cyanide. The key step of this strategy is represented by the synthesis of the enantiopure N-protected β-amino iodides 2 and 3 that are smoothly obtained from the parent amino alcohols 1 by polymer bound triarylphosphine-I2 complex in anhydrous dichloromethane.
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