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Published on: November 9, 2019
Stereoselective construction of eight-membered oxygen heterocycles by Brook rearrangement-mediated [3 + 4] annulation
Yuji Sawada1, Michiko Sasaki, Kei Takeda
1Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8551, Japan.
Abstract:
[reaction: see text] A newly developed strategy for eight-membered oxygen heterocycle construction via [3 + 4] annulation is described. The method involves the combination of beta-substituted acryloylsilanes and enolates of 6-oxacyclohept-2-en-1-one. A unique feature of this annulative approach is its capacity to generate eight-membered ring systems containing useful functionalities for further synthetic elaboration from readily available three- and four-carbon components.
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