1386412-91-4Relevant academic research and scientific papers
Asymmetric [3+2]-Cycloaddition of Morita-Baylis-Hillman Carbonates with Maleimides Catalyzed by Chiral Ferrocenylphosphines
Tu, Aiping,Hu, Haiwen,Du, Tieqi,Zhong, Weihui
, p. 3392 - 3399 (2014)
New chiral ferrocenylphosphines LB1-LB9 were designed and prepared through simple synthetic approaches. These air-stable ferrocenylphosphines were applied to promote asymmetric [3+2]-cycloaddition of Morita-Baylis-Hillman carbonates with maleimides, among which LB7 was shown to have good catalytic activity to afford the corresponding multifunctional cyclopentenes in up to 59% yield and up to 53% ee under mild reaction conditions. A plausible reaction mechanism was proposed.
Asymmetric [3+2] Cycloaddition of Olefins with Morita-Baylis-Hillman Carbonates Catalyzed by BINOL-Based Bifunctional Phosphine
Cui, Hai-Lei,Tang, Xue,Li, Meng-Fan,Xu, Xing-Jie,Shi, Yin
supporting information, p. 845 - 850 (2019/04/25)
We have developed a series of novel BINOL-based phosphines. These bifunctional organocatalysts can be used in the [3+2] cycloaddition of electron-deficient olefins and Morita-Baylis-Hillman (MBH) carbonates. Moderate to excellent yields (up to >99%) and good to excellent enantioselectivities (up to 95% ee) can be obtained in the cycloaddition reaction of maleimides and MBH carbonates. The application of these novel phosphines can be further extended to the asymmetric synthesis of chiral spirooxindoles (up to 85% ee). The results in this study indicate that the BINOL moiety plays an important role in stereocontrol.
Asymmetric construction of functionalized bicyclic imides via [3 + 2] annulation of MBH carbonates catalyzed by dipeptide-based phosphines
Zhong, Fangrui,Chen, Guo-Ying,Han, Xiaoyu,Yao, Weijun,Lu, Yixin
supporting information; experimental part, p. 3764 - 3767 (2012/08/28)
A highly enantioselective [3 + 2] annulation of MBH carbonates and maleimides catalyzed by chiral phosphines has been developed. In the presence of 5 mol % of l-Thr-l-Val-derived phosphine 6, functionalized bicyclic imides were prepared in excellent yields, and with high diastereoselectivities and nearly perfect enantioselectivities.
