Asymmetric Synthesis of 1-Benzazepine Derivatives via Copper-Catalyzed Intramolecular Reductive Cyclization

被引：23

作者：

Li, DingXi ^{[1
,2
]}

Park, Yeji ^{[1
,2
]}

Yoon, Woojin ^{[3
,4
]}

Yun, Hoseop ^{[3
,4
]}

Yun, Jaesook ^{[1
,2
]}

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 16419, South Korea

[2] Sungkyunkwan Univ, Inst Basic Sci, Suwon 16419, South Korea

[3] Ajou Univ, Dept Energy Syst Res, Suwon 16499, South Korea

[4] Ajou Univ, Dept Chem, Suwon 16499, South Korea

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 23期

基金：

新加坡国家研究基金会;

关键词：

TERTIARY ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; RECENT PROGRESS; KETONES; AMINES; REAGENTS; AGONIST; DESIGN;

D O I：

10.1021/acs.orglett.9b03853

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric construction of enantioenriched 2,3-substituted-1-benzazepine derivatives containing a cyclic tertiary amine moiety was developed by copper-catalyzed reductive intramolecular cyclization of (E)-dienyl arenes with a tethered ketimine. This protocol involves tandem chemo-, regio-, and enantioselective hydrocupration and asymmetric cyclization in the presence of a chiral bisphosphine-copper catalyst. Under mild conditions, a broad range of 1-benzazepine derivatives was obtained in good to high yields with high degrees of diastereoselectivity and enantioselectivity.

引用

页码：9699 / 9703

页数：5

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