Schmidt Johannes Philipp, Breit Bernhard
Institut für Organische Chemie , Albert-Ludwigs-Universität Freiburg , Albertstrasse 21 , 79104 Freiburg im Breisgau , Germany . Email:
Chem Sci. 2019 Jan 24;10(10):3074-3079. doi: 10.1039/c8sc05502e. eCollection 2019 Mar 14.
A stereodivergent and diastereoselective transition-metal-catalyzed intramolecular hydroamidation of allenes and alkynes furnishing δ-vinyl-lactams is reported. Employing a rhodium catalyst allowed for the selective synthesis of the -δ-lactam. Conversely, a palladium catalyst led to the formation of the -δ-lactam in high selectivity. The new method shows high functional group compatibility and assorted synthetic transformations were demonstrated as well as its utility for the enantioselective formal total syntheses of (-)-cermizine C and (-)-senepodine G.
报道了一种立体发散性和非对映选择性的过渡金属催化的丙二烯和炔烃分子内氢酰胺化反应，可生成δ-乙烯基内酰胺。使用铑催化剂可选择性合成-δ-内酰胺。相反，钯催化剂能以高选择性生成-δ-内酰胺。该新方法显示出高官能团兼容性，展示了各种合成转化及其在对映选择性形式全合成（-）-cermizine C和（-）-senepodine G中的应用。
