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

• DOI: 10.1021/acs.orglett.7b02916
• Publication Date: 2017-11-03T11:37:47Z
• Authors: Jiru Jia; Aimin Yu; Shanshan Ma; Youquan Zhang; Ke Li; Xiangtai Meng
• Keywords: Domino; Pyran; Benzothiophene

Solvent-controlled switchable domino reactions between 2-alkylidenebenzothiophene-3(2H)-ones and Morita–Baylis–Hillamn (MBH) carbonate were developed. All exhibited excellent regioselectivity, producing a broad spectrum of benzothiophene-fused α-pyran, 2,3-dihydrooxepine, oxatricyclodecene derivatives. Furthermore, [4 + 2], 3], related from identical substrates can be controlled.