Palladium-Catalyzed Asymmetric Allylic Allylation of Racemic Morita-Baylis-Hillman Adducts

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• 作者：Xubin Wang ; Dr. Xiaoming Wang ; Dr. Zhaobin Han ; Dr. Zheng Wang and Prof. Dr. Kuiling Ding
• 刊名：Angewandte Chemie International Edition
• 出版年：2017
• 出版时间：January 19, 2017
• 年：2017
• 卷：56
• 期：4
• 页码：1116-1119
• 全文大小：818K
• ISSN：1521-3773

文摘

A palladium-catalyzed asymmetric allyl–allyl cross-coupling of acetates of racemic Morita–Baylis–Hillman adducts and allylB(pin) has been developed using a spiroketal-based bis(phosphine) as the chiral ligand, thus affording a series of chiral 1,5-dienes bearing a vinylic ester functionality in good yields, high branched regioselectivities, and uniformly excellent enantioselectivities (95–99 % ee). Further synthetic manipulations of the allylation products provided novel ways for rapid access to a range of chiral polycyclic lactones and polycyclic lactams, as well as the antidepressant drug (−)-Paroxetine, in high optical purities.