1384288-64-5Relevant academic research and scientific papers
The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement - Opening process
Yu, Jin,Ko, Soo Y.
, p. 650 - 654 (2012)
(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.
