Hydrogen phthalates of (R)- and (S)-isopropylidene glycerol, obtainable from racemic isopropylidene glycerol by reaction with phthalic anhydride and successive resolution with (S)- and (R)-1-phenylethylamine or, alternatively, from (R)- and (S)-isopropylidene glycerol, were regarded as potential new resolving agents A range of important 1-arylethylamines was selected to test their resolving capability. In particular, trial resolutions were carried out using equivalent amounts of racemic amine and hydrogen phthalate of (R)-isopropylidene glycerol The salts of the S isomers selectively crystallized from methanol or 2-propanol allowing to recover the (S)-1-arylethylamines in high chemical and optical yields. Copyright
Isopropylidene glycerol hydrogen phthalate: a new resolving agent. Application to the resolution of 1-arylethylamines / M. Pallavicini, E. Valoti, L. Villa, O. Piccolo. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 7:4(1996), pp. 1117-1122. [10.1016/0957-4166(96)00117-6]
Isopropylidene glycerol hydrogen phthalate: a new resolving agent. Application to the resolution of 1-arylethylamines
M. PallaviciniPrimo
;E. ValotiSecondo
;
1996
Abstract
Hydrogen phthalates of (R)- and (S)-isopropylidene glycerol, obtainable from racemic isopropylidene glycerol by reaction with phthalic anhydride and successive resolution with (S)- and (R)-1-phenylethylamine or, alternatively, from (R)- and (S)-isopropylidene glycerol, were regarded as potential new resolving agents A range of important 1-arylethylamines was selected to test their resolving capability. In particular, trial resolutions were carried out using equivalent amounts of racemic amine and hydrogen phthalate of (R)-isopropylidene glycerol The salts of the S isomers selectively crystallized from methanol or 2-propanol allowing to recover the (S)-1-arylethylamines in high chemical and optical yields. CopyrightPubblicazioni consigliate
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