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

Title
The synthesis of (R,S)-reboxetine employing a tandem cyclic sulfate rearrangement - Opening process
Authors
Yu J.Ko S.Y.
Ewha Authors
고수영
SCOPUS Author ID
고수영scopus
Issue Date
2012
Journal Title
Tetrahedron Asymmetry
ISSN
0957-4166JCR Link
Citation
vol. 23, no. 9, pp. 650 - 654
Indexed
SCI; SCIE; SCOPUS WOS scopus
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. © 2012 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.tetasy.2012.04.018
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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