Palladium-catalyzed highly atom-economical allylation of oxindoles with vinyl cyclopropanes

被引：14

作者：

Cao, Ruwei ^{[1
,2
]}

Zhang, Jinlong ^{[1
]}

Zhou, Hui ^{[1
,2
]}

Yang, Huameng ^{[1
]}

Jiang, Gaoxi ^{[1
,3
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Chinese Acad Sci, Suzhou Inst Nanotech & Nanobion, Div Adv Nanomat, Suzhou 215123, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 07期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE 3+2 CYCLOADDITION; ASYMMETRIC ALLYLIC ALKYLATION; SYNTHETIC REACTIONS; ALLYLBORONIC ACIDS; VINYLCYCLOPROPANES; CONSTRUCTION; PHYSOSTIGMINE; SUBSTITUTION; NUCLEOPHILES; SPIROKETALS;

D O I：

10.1039/c5ob02653a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly atom-economical allylation of oxindoles with vinyl cyclopropanes catalyzed by Pd(PPh3)(4) has been developed, setting up a practical venue for the installation of an all-carbon quaternary center at the 3-position in oxindoles under mild reaction conditions. Importantly, the reaction proceeded well without any additives and no waste was produced, affording linear products with high regioselectivities (>20:1). Enantioselective allylic alkylation has also been realized to provide the desired products in good yields and 35% ee.

引用

页码：2191 / 2194

页数：4

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