Enantioselective Alkylation of Aldehydes with Organoborons Enabled by Nickel/N-Heterocyclic Carbene Catalysis  

作　　者：Song-Yang Liu Zi-Chao Wang Shi-Liang Shi 

机构地区：[1]College of Chemistry and Material Science,Shanghai Normal University,100 Guilin Road,Shanghai 200234,China [2]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of rganic Chemitry,University of Chinee Academy of Scienc Chinese Academy of Sciences,345 Lingling Road,Shanghai 200032,China

出　　处：《Chinese Journal of Chemistry》2024年第18期2161-2165,共5页中国化学（英文版）

基　　金：supported by the National Key R&D Program of China(2022YFA1503702,2021YFF0701600);the National Natural Science Foundation of China(22325110,92256303,21821002,22171280);the Strategic Priority Research Program of the Chinese Academy of Sciences(XDB0610000);the Program of Shanghai Academic Research Leader(22XD1424900);the CAS Youth Interdisciplinary Team(JCTD-2021-11)and the Ningbo Natural Science Foundation(2022J017).

摘　　要：Transition-metal-catalyzed asymmetric alkylation of aldehydes represents a straightforward strategy for the synthesis of chiral secondary alcohols.However,efficient methods using organoborons as coupling reagents are rare.Herein,we report a highly enantioselective nickel-catalyzed alkylation reaction of aldehydes,using readily available alkylborons as nucleophiles.A wide variety of chiral secondary alcohols were prepared from commercially available aldehydes with high yields.The key to the excellent enantioselectivity and chemoselectivity was the employment of a bulky C2-symmetric chiral NHC ligand.This protocol features excellent enantiocontrol,mild conditions,and good functional group compatibility.

关 键 词：Enantioselective alkylation Nickel catalysis N-Heterocyclic carbene Organoborons Chiral alcohols Asymmetric catalysis C-C coupling Synthetic methods 

分 类 号：O62[理学—有机化学]