通过膦催化的烯酸酯β,γ-环化反应对环戊烷进行对映选择性合成。
Enantioselective Synthesis of Cyclopentanes by Phosphine-Catalyzed β,γ-Annulation of Allenoates.
作者信息
Zhang Chenxi, Maddigan-Wyatt Jeremy T, Nguyen Xuan, Seitz Antonia, Breugst Martin, Lupton David W
机构信息
School of Chemistry, Monash University, Clayton 3800, Victoria, Australia.
Institut für Chemie, Technische Universität Chemnitz, Straße der Nationen, 09111 Chemnitz, Germany.
出版信息
Org Lett. 2024 Sep 20;26(37):7800-7804. doi: 10.1021/acs.orglett.4c02371. Epub 2024 Sep 6.
Herein, we report the enantioselective phosphine-catalyzed β,γ-annulation of electron-poor allenes with bifunctional malonates. The reaction exploits a 2C phosphonium synthon that when accessed using ()-SITCP gives 23 cyclopentanes with high stereoselectivity (most >95:5 er and >9:1 dr) and yield. In addition to the (3+2) annulation, a one-pot three-component variant to give the same cyclopentanes and a (3+2) annulation/Dieckmann cyclization cascade, along with mechanistic studies, are reported.
在此，我们报道了贫电子丙二烯与双功能丙二酸酯的对映选择性膦催化β,γ-环化反应。该反应利用了一种2C磷鎓合成子，当使用()-SITCP时，可得到23种具有高立体选择性（大多数对映体过量>95:5且非对映体比例>9:1）和产率的环戊烷。除了(3 + 2)环化反应外，还报道了一种一锅三组分变体以得到相同的环戊烷以及一种(3 + 2)环化/迪克曼环化级联反应，并进行了机理研究。
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