Concise Report
Enantioselective Alkylation of Aldehydes with Organoborons Enabled by Nickel/N-Heterocyclic Carbene Catalysis†
Song-Yang Liu,
Zi-Chao Wang,
Shi-Liang Shi,
Song-Yang Liu
College of Chemistry and Material Science, Shanghai Normal University, 100 Guilin Road, Shanghai, 200234 China
Search for more papers by this authorCorresponding Author
Zi-Chao Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
E-mail: [email protected], [email protected]Search for more papers by this authorCorresponding Author
Shi-Liang Shi
College of Chemistry and Material Science, Shanghai Normal University, 100 Guilin Road, Shanghai, 200234 China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
E-mail: [email protected], [email protected]Search for more papers by this authorSong-Yang Liu,
Zi-Chao Wang,
Shi-Liang Shi,
Song-Yang Liu
College of Chemistry and Material Science, Shanghai Normal University, 100 Guilin Road, Shanghai, 200234 China
Search for more papers by this authorCorresponding Author
Zi-Chao Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
E-mail: [email protected], [email protected]Search for more papers by this authorCorresponding Author
Shi-Liang Shi
College of Chemistry and Material Science, Shanghai Normal University, 100 Guilin Road, Shanghai, 200234 China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
E-mail: [email protected], [email protected]Search for more papers by this author†
Dedicated to the Special Issue of Nickel Catalysis.
Comprehensive Summary
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.
Supporting Information
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| cjoc202400288-sup-0001-supinfo.pdfPDF document, 7.9 MB |
Appendix S1: Supporting Information |
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