1412913-04-2Relevant academic research and scientific papers
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.
Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates with maleimides
Deng, Hong-Ping,Wang, De,Wei, Yin,Shi, Min
supporting information; experimental part, p. 1098 - 1104 (2012/09/07)
We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with maleimides, which can efficiently construct functionalized cyclopentenes bearing three contiguous stereocenters in moderate to excellent yields and excellent diastereo- and enantioselectivities. A plausible mechanism has been also proposed on the basis of control experiments and previous literature.
