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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
Author(s) -
De Risi Carmela,
Perrone Daniela,
Dondoni Alessandro,
Pollini Gian Piero,
Bertolasi Valerio
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200698
Subject(s) - chemistry , phosphonate , trifluoromethanesulfonate , silylation , stereoselectivity , alkoxy group , organic chemistry , primary (astronomy) , adduct , medicinal chemistry , alkyl , catalysis , physics , astronomy
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)