Ir-Catalyzed Enantioselective Intra- and Intermolecular Formal C-H Conjugate Addition to β-Substituted α,β-Unsaturated Esters

被引：31

作者：

Shibata, Takanori ^{[1
]}

Kurita, Hisaki ^{[1
]}

Onoda, Sahoko ^{[1
]}

Kanyiva, Kyalo Stephen ^{[2
]}

机构：

[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, 3-4-1 Okubo, Tokyo 1698555, Japan

[2] Waseda Univ, Sch Adv Sci & Engn, Global Ctr Sci & Engn, Shinjuku Ku, 3-4-1 Okubo, Tokyo 1698555, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 07期

关键词：

acrylates; C-H alkylation; conjugate addition; enantioselectivity; iridium; BOND ALKYLATION; AROMATIC AMIDES; ACTIVATION; HETEROCYCLES; ANNULATION; ACRYLATES; ALKENES; KETONES;

D O I：

10.1002/ajoc.201800257

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective intramolecular formal C-H conjugate addition of 4-methyl 1-aryl 2-methylfumarates proceeded using a chiral iridium catalyst. A benzoylamide group served as a directing group, and chiral gamma-lactones with a quaternary all-carbon stereogenic center were obtained with up to excellent ee. In the intermolecular reaction of N-arylbenzamides with beta-substituted acrylates, C-H bond activation selectively occurred at the ortho-position of carbonyl groups, and highly enantioselective formal C-H conjugate addition proceeded.

引用

页码：1411 / 1418

页数：8

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