Enantioselective synthesis of 3-substituted-4-aryl piperidines useful for the preparation of paroxetine |
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Authors: | KSKeshava Murthy Allan W Rey Michael Tjepkema |
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Institution: | Brantford Chemicals Inc., 34 Spalding Drive, Brantford, Ontario, Canada N3T 6B8 |
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Abstract: | The asymmetric conjugate addition reaction between 4-fluorophenylmagnesium bromide and various chiral α,β-unsaturated esters and enoylsultam substrates was explored to prepare a key intermediate useful in the preparation of paroxetine. The most selective auxiliary was found to be Oppolzer's (1S)-(−)-camphorsultam. Interestingly, the diastereoselection was opposite to that reported for acyclic enoylsultams. |
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Keywords: | Michael reaction asymmetric synthesis paroxetine Grignard addition camphorsultam |
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