TY - JOUR
T1 - The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement - Opening process
AU - Yu, Jin
AU - Ko, Soo Y.
PY - 2012/5/15
Y1 - 2012/5/15
N2 - (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.
AB - (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.
UR - http://www.scopus.com/inward/record.url?scp=84862691331&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2012.04.018
DO - 10.1016/j.tetasy.2012.04.018
M3 - Article
AN - SCOPUS:84862691331
SN - 0957-4166
VL - 23
SP - 650
EP - 654
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 9
ER -