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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Stereoselective construction of eight-membered carbocycles by brook rearrangement-mediated [3 + 4] annulation
Kei Takeda1, Yuji Sawada, Koichi Sumi
1Institute of Pharmaceutical Sciences, Faculty of Medicine, Hiroshima University, 1-2-3 Kasumi, Hiroshima 734-8551, Japan. takedak@hiroshima-u.ac.jp
Abstract:
[reaction: see text] A newly developed strategy for eight-membered carbocycles via [3 + 4] annulation that involves the combination of beta-substituted acryloylsilanes and enolates of cycloheptenone is described. A unique feature of this annulative approach is its capacity to generate, in two steps, eight-membered ring systems containing useful functionalities for further synthetic elaboration from readily available three- and four-carbon components.
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