The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement - Opening process

Jin Yu, Soo Y. Ko

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

(R,S)-Reboxetine was synthesized in nine steps and with 43% overall yield starting from trans-cinnamyl alcohol. Following silylation and AD steps, the two hydroxyl groups at C-1 and C-2 were simultaneously activated to the cyclic sulfate. A series of tandem reactions initiated by desilylation transposed the activation to C-3, then to C-1, where nucleophilic displacements took place in succession. During this process, the configuration at C-2 was inverted while that at C-1 was retained through a double inversion.

Original languageEnglish
Pages (from-to)650-654
Number of pages5
JournalTetrahedron Asymmetry
Volume23
Issue number9
DOIs
StatePublished - 15 May 2012

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