A New and Expedient Diastereoselective Synthesis of α-(Hydroxyamino)phosphonates and α-Aminophosphonates by Silyl Triflate Promoted Diethyl Phosphite Addition to Chiral N-Benzyl Nitrones

✍ Scribed by Carmela De Risi; Daniela Perrone; Alessandro Dondoni; Gian Piero Pollini; Valerio Bertolasi

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 270 KB
• Volume: 2003
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200200698

✦ Synopsis

Abstract

An efficient methodology for the synthesis of α‐aminophosphonates has been developed taking advantage of the tert‐butyldimethylsilyl triflate activated addition of diethyl phosphite to N‐benzyl nitrones derived from chiral α‐alkoxy and α‐(Boc‐amino) aldehydes. The stereoselective carbon− phosphorus bond‐forming reaction proceeded smoothly to give α‐(hydroxyamino)phosphonate intermediates as the primary adducts, which were subsequently converted into the corresponding polyhydroxylated α‐amino‐ and α,β‐diaminophosphonates by conventional reductive processes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)