Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany).
Technische Universität Dortmund, Fakultät Chemie und Chemische Biologie, Chemische Biologie, Otto-Hahn-Strasse 6, 44227 Dortmund (Germany).
Angew Chem Int Ed Engl. 2015 Jun 22;54(26):7653-6. doi: 10.1002/anie.201502233. Epub 2015 May 8.
We report a rhodium(II)-catalyzed highly enantioselective 1,3-dipolar cycloaddition reaction between the carbonyl moiety of tropone and carbonyl ylides to afford troponoids in good to high yields with excellent enantioselectivity. We demonstrate that α-diazoketone-derived carbonyl ylides, in contrast to carbonyl ylides derived from diazodiketoesters, undergo [6+3] cycloaddition reactions with tropone to yield the corresponding bridged heterocycles with excellent stereoselectivity.
我们报告了铑（II）催化的高对映选择性 1,3-偶极环加成反应，该反应在羰基部分的热带酮和羰基叶立德之间进行，以优异的对映选择性得到良好至高产率的 tropone 类似物。我们证明，与二酮酯衍生的羰基叶立德相比，α-重氮酮衍生的羰基叶立德与热带酮进行 [6+3] 环加成反应，以优异的立体选择性生成相应的桥杂环。
