Enantioselective Alkylation of Aldehydes with Organoborons Enabled by Nickel/N-Heterocyclic Carbene Catalysis
Song-Yang Liu , Zi-Chao Wang , Shi-Liang Shi
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (18) : 2161 -2165.
Enantioselective Alkylation of Aldehydes with Organoborons Enabled by Nickel/N-Heterocyclic Carbene Catalysis
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 C 2-symmetric chiral NHC ligand. This protocol features excellent enantiocontrol, mild conditions, and good functional group compatibility.
Enantioselective alkylation / Nickel catalysis / N-Heterocyclic carbene / Organoborons / Chiral alcohols / Asymmetric catalysis / C—C coupling / Synthetic methods
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
