A Tandem Olefin Migration and Prins Cyclization Using Cu(OTf)(2)-Bisphosphine Complexes: An Improved Synthesis of Functionalized Tetrahydropyrans |
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| Authors: | Ghosh Arun K Nicponski Daniel R Kass Jorden |
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| Institution: | Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, United States |
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| Abstract: | In situ-generated (bis-DPPMB)-Cu(OTf)2 complex has been examined to catalyze a tandem olefin migration and Prins cyclization of an alkenol with various aldehydes. The reaction proceeded with electron-rich aromatic aldehydes at room temperature and provided functionalized tetrahydropyrans in good yields. An efficient synthesis of the bis-DPPMB ligand has also been described. |
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| Keywords: | Phosphine ligand Prins cyclization Phosphine-borane adduct Tetrahydropyrans Prins chemistry |
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