Abstract
LY503430, an optically active β-fluoroamine, is a potential therapeutic agent for the Parkinson's disease. Different strategies have been studied to synthesize this molecule using a regioselective and stereospecific rearrangement of β-amino alcohols into β-fluoroamines induced by DAST. This reaction allowed the synthesis of LY503430 with an excellent enantiomeric excess.
Highlights
LY503430, an optically active β-fluoroamine, which is a potential therapeutic agent for the Parkinson’s disease,[1] has been prepared by Eli Lilly on gram scale[2] as well as on a kilogram scale[2] from racemic β-fluoroamine (±)-A
We have reported that N,N-dialkyl β-amino alcohols B can be enantioselectively and regioselectively rearranged to β-fluoroamines C by treatment with N,N-diethylaminosulfur trifluoride (DAST)[3] in excellent yield and enantiomeric excess (Scheme 2).[4]
The synthesis of β-fluoroamine D has been envisaged by utilizing an enantioselective rearrangement of β-amino alcohol E induced by DAST
Summary
LY503430, an optically active β-fluoroamine, which is a potential therapeutic agent for the Parkinson’s disease,[1] has been prepared by Eli Lilly on gram scale[2] as well as on a kilogram scale[2] from racemic β-fluoroamine (±)-A. We have reported that N,N-dialkyl β-amino alcohols B can be enantioselectively and regioselectively rearranged to β-fluoroamines C by treatment with N,N-diethylaminosulfur trifluoride (DAST)[3] in excellent yield and enantiomeric excess (Scheme 2).[4]. Stereospecific rearrangement of β-amino alcohols B to fluoroamines C. We would like to report our synthetic efforts toward the synthesis of LY503430 by considering the rearrangement of β-amino alcohols B as the key step to introduce the β-fluoroamino moiety present in LY503430. Our efforts have culminated to the total synthesis of this biologically active compound.[4]
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