Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers

被引:16
|
作者
Das, Arko [1 ]
Joshi, Harshit [1 ]
Singh, Vinod K. [1 ]
机构
[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
NITROGEN-HETEROCYCLES; PHARMACEUTICALS; NUCLEOPHILES; ADDITIONS; ENALS;
D O I
10.1021/acs.orglett.1c03626
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective approach for synthesizing fluorinated azaarenes containing vicinal quaternary-tertiary stereocenters is summarized. The chiral copper(I)-phosphine complex binds with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in alpha-functionalized products with an excellent level of enantioselectivities (up to 99%), diastereoselectivities (>20:1), and yields (up to 97%). Furthermore, post-functionalization of the acyl imidazole part has also been demonstrated.
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收藏
页码:9441 / 9445
页数:5
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