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Published on: February 7, 2019
Stereoselective synthesis of 2,8-dioxabicyclo[3.3.1]nonane derivatives via a sequential Michael
Guodong Yin1, Tianbing Ren, Yin Rao
1Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, PR China. gdyin@hbnu.edu.cn
Abstract:
A highly efficient and stereoselective synthesis of coumarin-, 1,3-cyclohexanedione-, and 1,4-naphthoquinone-fused 2,8-dioxabicyclo[3.3.1]nonanes is described. This was achieved via a sequential Michael addition/bicyclization reaction from easily accessible 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one derivatives. Three chemical bonds (one C-C bond and two C-O bonds), two six-membered cycles, and two stereogenic centers were formed in a one-pot operation.
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