Modular Synthesis of Multi-substituted Cyclobutanones Enabled by Oxyallyl Cations†
Meng Wang
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433 China
Present address: Department of Cancer Biology, Dana-Farber Cancer Institute; Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, MA 02115, USA
Search for more papers by this authorZhonggui Wang
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433 China
Search for more papers by this authorCorresponding Author
Ping Lu
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433 China
E-mail: [email protected]Search for more papers by this authorMeng Wang
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433 China
Present address: Department of Cancer Biology, Dana-Farber Cancer Institute; Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, MA 02115, USA
Search for more papers by this authorZhonggui Wang
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433 China
Search for more papers by this authorCorresponding Author
Ping Lu
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433 China
E-mail: [email protected]Search for more papers by this authorDedicated to the Memory of Professor Xiyan Lu.
Comprehensive Summary
Stereoselective synthesis of multi-substituted cyclobutanes with different substituents is still a daunting challenge in organic synthesis. We report here a practical and facile approach to synthesizing all-trans 2,3,4-trisubstituted cyclobutanones from readily available dichlorocyclobutanones. The substitution reaction proceeds smoothly via oxyallyl cation intermediates under mild basic conditions. Further transformation to the synthesis of 1,2,3,4-tetrasubstituted cyclobutanes was also explored.
Supporting Information
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