Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

被引：11

作者：

Manna, Kartic ^{[1
,2
]}

Begam, Hasina Mamataj ^{[1
]}

Samanta, Krishanu ^{[1
,2
]}

Jana, Ranjan ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Chem Biol, Organ & Med Chem Div, Kolkata 700032, W Bengal, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 19期

关键词：

SERIAL LIGAND CATALYSIS; C-H ACTIVATION; BOND ACTIVATION; PALLADIUM; ALKYLATION; OLEFINS; FUNCTIONALIZATION; ALKENES; MILD;

D O I：

10.1021/acs.orglett.0c02465

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the beta-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

引用

页码：7443 / 7449

页数：7

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