Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α‑Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives

Solvent-controlled switchable domino reactions between 2-alkylidenebenzothiophene-3­(2H)-ones and Morita–Baylis–Hillamn (MBH) carbonate were developed. All domino reactions exhibited excellent regioselectivity, producing a broad spectrum of benzothiophene-fused α-pyran, 2,3-dihydrooxepine, and oxatr...

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Bibliographic Details
Published in:Organic letters 2017-11, Vol.19 (22), p.6084-6087
Main Authors: Jia, Jiru, Yu, Aimin, Ma, Shanshan, Zhang, Youquan, Li, Ke, Meng, Xiangtai
Format: Article
Language:English
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Summary:Solvent-controlled switchable domino reactions between 2-alkylidenebenzothiophene-3­(2H)-ones and Morita–Baylis–Hillamn (MBH) carbonate were developed. All domino reactions exhibited excellent regioselectivity, producing a broad spectrum of benzothiophene-fused α-pyran, 2,3-dihydrooxepine, and oxatricyclodecene derivatives. Furthermore, [4 + 2], [4 + 3], and related domino reactions from identical substrates can be controlled.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02916