Abstract
(Cyanomethylene)tributylphosphorane (CMBP) can promote the Mitsunobu reaction of 1,3- and 1,5-diols with N-nonsubstituted sulfonamides, such as tosylamide (TsNH2) and 3,3-dimethoxypropylsulfonamide (DimpsNH2), to prepare azetidine and piperidine ring systems directly. Utilizing this methodology, lupinine, a biologically active piperidine alkaloid, was synthesized.
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CITATION STYLE
Kaku, H., Sonoda, Y., Hishida, H., Taniguchi, Y., Kubo, A., Hamaguchi, T., … Tsunoda, T. (2019). Piperidine and azetidine formation by direct cyclization of diols with N-nonsubstituted sulfonamide under the Mitsunobu conditions utilizing (cyanomethylene)tributylphosphorane (CMBP) and its application to the synthesis of lupinine. Heterocycles, 98(11), 1525–1535. https://doi.org/10.3987/COM-19-14171
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