Abstract
A method for enantioselective desymmetrization of N-Ac and N-Boc-FTY720 by nonenzymatic asymmetric acylation was developed. Effective enantioselective monobenzoylation using benzoyl chloride in the presence of the tetraphenylbisoxazoline (L2)-CuCl2 complex gave the desired products 3a and 3b in 52-62% yield with 64% ee.
MeSH terms
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Acylation
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Benzoates / chemistry
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Catalysis
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Coordination Complexes / chemistry
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Copper / chemistry
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Fingolimod Hydrochloride
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Oxazoles / chemistry
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Propylene Glycols / chemistry*
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Solvents / chemistry
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Sphingosine / analogs & derivatives*
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Sphingosine / chemistry
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Stereoisomerism
Substances
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Benzoates
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Coordination Complexes
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Oxazoles
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Propylene Glycols
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Solvents
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Copper
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Fingolimod Hydrochloride
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Sphingosine
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cupric chloride
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benzoyl chloride