Diastereoselective synthesis of β-amino-α-hydroxy phosphonates via oxazaborolidine catalyzed reduction of β-phthalimido-α-keto phosphonates

• Published in: Tetrahedron letters Vol. 40; no. 43; pp. 7705 - 7708
• Main Authors: Barco, Achille, Benetti, Simonetta, Bergamini, Paola, De Risi, Carmela, Marchetti, Paolo, Pollini, Gian P., Zanirato, Vinicio
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 22.10.1999; Elsevier
• Subjects: amino acid derivatives; amino acids; Arbuzov reaction; Chemistry; Chemistry, Organic; phosphonic acid derivatives; phosphonic acids; Physical Sciences; Science & Technology; Arbuzov reaction; phosphonic acids; amino acid derivatives; phosphonic acid derivatives; amino acids; ACID
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(99)01573-7

Reduction of β-phthalimido-α-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded β-phthalimido-α-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds. Graphic