288314-67-0Relevant articles and documents
Towards enantiomeric 2,3-epoxypropylphosphonates
Wroblewski, Andrzej E.,Halajewska-Wosik, Anetta
, p. 2053 - 2055 (2000)
Hydrolysis of diethyl 2,3-epoxypropylphosphonate in the presence of (R,R)-salen-Co(III)-OAc after 19 h afforded a mixture of (S)-epoxide (82% ee) and diethyl (R)-2,3-dihydroxypropylphosphonate (98% ee). Improved enantiomeric excess (93%) of the (S)-epoxide was obtained in the 72 h hydrolytic kinetic resolution experiment. Acid-catalyzed hydrolysis of (S)-epoxide (91% ee) gave (S)-diol (72% ee) due to low C-3 regioselectivity of the reaction. Copyright (C) 2000 Elsevier Science Ltd.
An efficient synthesis of enantiomeric (S)-phosphocarnitine
Wroblewski, Andrzej E.,Halajewska-Wosik, Anetta
, p. 2758 - 2763 (2002)
Diethyl (S)-2,3-epoxypropylphosphonate [(S)-3] was transformed into (S)-phosphocarnitine [(S)-2] in the following sequence of reactions: a C-3 regioselective opening of the oxirane ring with magnesium bromide, quantitative bromide displacement with trimethylamine, and ester hydrolysis. The epoxide ring opening of 3 with HC1/EtOAc gave a 92:8 mixture of 3- and 2-chloro-substituted phosphonates, Reaction of (S)-3 with aqueous NMe3 gave diethyl 3-hydroxy-l-propenylphosphonate as a major product. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
