Rhodium‐Catalyzed Desymmetrization by Hydroformylation of Cyclopentenes: Synthesis of Chiral Carbocyclic Nucleosides

作者：Cai You, Biao Wei, Xiuxiu Li, Yusheng Yang, Na Li, Hui Lv, Xumu Zhang · 发表于：Angewandte Chemie International Edition · 年份：2016 · DOI：10.1002/anie.201601478 · 被引用次数：51 · 研究领域：Asymmetric Hydrogenation and Catalysis、Organometallic Complex Synthesis and Catalysis、Cyclopropane Reaction Mechanisms

Excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (up to >99:1 d.r.) have been achieved in the desymmetrization of cyclopentenes by catalytic hydroformylation. This novel methodology provides an efficient and concise synthetic route to chiral cyclopentane carboxaldehydes. The key intermediate, (1S,3S)-(3-hydroxymethyl)cyclopentanol, for the synthesis of carbocyclic-ddA was obtained in three steps.