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Beilstein J. Org. Chem. 2014, 10, 3038–3055, doi:10.3762/bjoc.10.322
Graphical Abstract
Scheme 1: Chemoenzymatic synthesis of enantioenriched enantiomers of promethazine 9 and ethopropazine 10. Rea...
Figure 1: Dependence of optical purities (% ee) of (R)-(−)-6a (red curve, ■) and (S)-(+)-5 (blue curve, ▲) on...
Scheme 2: Assignment of the stereochemistry of enantiopure alcohol (+)-5 resulting from derivatization with (R...
Figure 2: Description of substituents for determination of the absolute configuration of (+)-5 and ΔδRS value...
Figure 3: 1H NMR (CDCl3, 400 MHz) spectra of the (R)-MPA 11 (red colored line) and (S)-MPA and 12 (blue color...
Figure 4: An ORTEP plot of (S)-(+)-1-(10H-phenothiazin-10-yl)propan-2-ol (S)-(+)-5. The following crystal str...
Scheme 3: Amination of optically active bromo derivatives (R)-(+)-8 or (S)-(−)-8 in toluene.
Scheme 4: Amination of optically active bromo derivatives (R)-(+)-8 or (S)-(−)-8 in methanol.
Scheme 5: The proposed reaction mechanism for amination of optically active (S)-(−)-8 in methanol.
Beilstein J. Org. Chem. 2013, 9, 516–525, doi:10.3762/bjoc.9.56
Scheme 1: Synthesis of optically active ILs. Reagents and conditions: (i) 1,2-propylene oxide (1.1 equiv), 32...
Scheme 2: Conversion of (+)-5a and (+)-5b into MPA esters 9a, 9b and 10a, 10b.
Figure 1: Model for the configurational correlation of MPA esters 9a, 9b and 10a, 10b.
Figure 2: The 1H NMR spectra of the derivatives of two unreacted chiral alcohols (+)-5a (top) and (+)-5b (bot...