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Synthesis of enantiomerically pure (d) – doxylamine using a novel chiral auxiliary


Christabel Nang’andu Hikaambo
Hanzooma Hatwiko
Derick Munkombwe
Aubrey Chichonyi Kalungia
Chiluba Mwila
Steward Mudenda
Ronald Kampamba Mutati
Martin Kampamba
Hee Doo Kim

Abstract

It is known that the main mode of synthesis of doxylamine is a racemic mixture. However, the active enantiomers of the compound show superior activity to that of the racemate, thus the need to synthesize doxylamine as an enantiopure compound. This study aimed to synthesise an enantiopure (d)-doxylamine and it was achieved through the use of optically active diols synthesised from a novel chiral auxiliary. While most available methods employ Sharpless asymmetric dihydroxylation, this study reports a method that achieves superior enantiomeric excess with consequent better yields of 67% of end products not easily accessible by use of Sharpless Asymmetric Dihydroxylation.


Journal Identifiers


eISSN: 1997-342X
print ISSN: 1991-8631