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Enantioselective synthesis of 3-substituted-4-aryl piperidines useful for the preparation of paroxetine

✍ Scribed by K.S.Keshava Murthy; Allan W Rey; Michael Tjepkema

Book ID: 104253866
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 223 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01192-4

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✦ Synopsis

The asymmetric conjugate addition reaction between 4-fluorophenylmagnesium bromide and various chiral a,b-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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