Asymmetric Rh(I)-Catalyzed Functionalization of the 3-C(sp(3))-H Bond of Benzofuranones with alpha-Diazoesters

作者：Liu, Yuanhong; Zhou, Chao; Xiong, Miao; Jiang, Jijun; Wang, Jun^*

来源：Organic Letters, 2018, 20(18): 5889-5893.

DOI：10.1021/acs.orglett.8b02555

An asymmetric Rh(I)-catalyzed functionalization of the 3-C(sp(3))-H bond of benzofuranones with alpha-diazoesters has been developed, providing a new strategy for the stereoselective 3-alkylation of benzofuranones. With low catalyst loadings (low to 0.02 mol % Rh), a number of benzofuranones bearing consecutive quaternary and tertiary stereogenic centers have been synthesized (up to 94% yield, 95:5 dr, and >99% ee). The synthetic utilities of this methodology have been demonstrated by elaborating the model product 3aa to a series of enantiopure compounds with similarities to natural products and drug candidates.

• 出版日期2018-9-21
• 单位中山大学