Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution

被引：24
|
作者：
Touge, Taichiro [1 ]
Nara, Hideki [1 ]
Kida, Michio [1 ]
Matsumura, Kazuhiko [1 ]
Kayaki, Yoshihito [2 ]
机构：
[1] Takasago Int Corp, Corp Res & Dev Div, Hiratsuka, Kanagawa 2540073, Japan
[2] Tokyo Inst Technol, Sch Mat & Chem Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo 1528552, Japan
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 08期
关键词：
ENANTIOSELECTIVE SYNTHESIS; REDUCTION; HALOHYDRINS; RECEPTOR; INTERMEDIATE; DERIVATIVES; ALCOHOLS; ACCESS;
D O I：
10.1021/acs.orglett.1c00739
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient dynamic kinetic resolution of cyclic halohydrins was achieved by the asymmetric transfer hydrogenation of racemic alpha-haloketones. Bifunctional oxo-tethered Ru(II) catalysts could promote the reduction without deterioration of halogens. By structural tuning of the catalyst, chiral alcohols having halogen, ester, carboxamide, and sulfone functions were obtained variably with excellent diastereo- and enantioselectivities (up to >99:1 d.r. and >99.9 ee), which provided a concise synthetic approach to a dopamine D3 receptor ligand, (+)-PHNO.
引用
收藏
页码：3070 / 3075
页数：6
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