title: Synthesis of the rac-6-hydroxy-3-methoxycyclohex-2-enone and resolution through recrystallization of its diastereomeric N-tosyl-(S)-proline esters
abstract: The synthesis and resolution of rac-6-hydroxy-3-methoxycyclohex-2-enone, by fractional crystallization of diastereomeric esters of N-protected (S)-proline was shown to be an effective method for preparation of both pure diastereomers (>95% d.e., according to (1)H NMR data). The absolute configuration of the asymmetric center in cyclohexene ring was determined based on the inversed octant rule for the sign of circular dichroism for these cyclohexenones (n-pi*-transition band at approximately 300 nm) and further substantiated by chemical conversion of the (-)-(6R,2'S)-diastereomer into the known (+)-(R)-4-hydroxycyclohex-2-enone. Copyright 2000 Wiley-Liss, Inc.
authors.affiliation: Institute of Bio-Organic Chemistry, National Academy of Science, Minsk, Belarus.
authors.initials: VG
authors.lastname: Zaitsev
authors.initials: DG
authors.lastname: Sachava
authors.initials: GS
authors.lastname: Yankovskaya
authors.initials: NI
authors.lastname: Garbuz