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1 article(s) from Paprocki, Daniel

First chemoenzymatic stereodivergent synthesis of both enantiomers of promethazine and ethopropazine

Paweł Borowiecki,
Daniel Paprocki and
Maciej Dranka

Beilstein J. Org. Chem. 2014, 10, 3038–3055, doi:10.3762/bjoc.10.322

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Scheme 1: Chemoenzymatic synthesis of enantioenriched enantiomers of promethazine 9 and ethopropazine 10. Rea...

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Figure 1: Dependence of optical purities (% ee) of (R)-(−)-6a (red curve, ■) and (S)-(+)-5 (blue curve, ▲) on...

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Scheme 2: Assignment of the stereochemistry of enantiopure alcohol (+)-5 resulting from derivatization with (R...

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Figure 2: Description of substituents for determination of the absolute configuration of (+)-5 and Δδ^RS value...

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Figure 3: ¹H NMR (CDCl₃, 400 MHz) spectra of the (R)-MPA 11 (red colored line) and (S)-MPA and 12 (blue color...

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Figure 4: An ORTEP plot of (S)-(+)-1-(10H-phenothiazin-10-yl)propan-2-ol (S)-(+)-5. The following crystal str...

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Scheme 3: Amination of optically active bromo derivatives (R)-(+)-8 or (S)-(−)-8 in toluene.

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Scheme 4: Amination of optically active bromo derivatives (R)-(+)-8 or (S)-(−)-8 in methanol.

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Scheme 5: The proposed reaction mechanism for amination of optically active (S)-(−)-8 in methanol.

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Published 18 Dec 2014

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