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

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 24期

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.

引用

页码：9441 / 9445

页数：5

共 49 条

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Synthese enantiomerenangereicherter, vicinaler tertiärer und quartärer Kohlenstoff-Stereozentren innerhalb einer acyclischen Kette
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