Copper-Catalyzed Chemoselective Asymmetric Hydrogenation of C=O Bonds of Exocyclic α,β-Unsaturated Pentanones,Angewandte Chemie International Edition

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Copper-Catalyzed Chemoselective Asymmetric Hydrogenation of C=O Bonds of Exocyclic α,β-Unsaturated Pentanones
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2023-06-12 , DOI: 10.1002/anie.202306380
Jing Guan ₁ , Jianzhong Chen ₁ , Yicong Luo ₁ , Lisen Guo ₁ , Wanbin Zhang ₁

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An earth-abundant transition-metal copper catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated pentanones affording the corresponding chiral exocyclic allylic pentanols in up to 99 % yield and 96 % ee (enantiomeric excess) is reported. Mechanistic studies indicate that only the C=O bond is chemoselectively reduced and the reaction is promoted via the multiple attractive dispersion interactions between the Cu catalyst and substrate.

中文翻译：

铜催化环外α,β-不饱和戊酮C=O键的化学选择性不对称氢化

据报道，地球丰富的过渡金属铜催化环外 α,β-不饱和戊酮的不对称氢化，得到相应的手性环外烯丙基戊醇，收率高达 99%，ee（对映体过量）为 96%。机理研究表明，只有 C=O 键被化学选择性还原，并且通过 Cu 催化剂和底物之间的多重吸引分散相互作用促进反应。

更新日期：2023-06-12

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