Oxa-diels-alder reaction of isatins and acyclic α,β-unsaturated methyl ketones through cooperative dienamine and metal lewis acid catalysis

Lu Liu; Philias Daka; Ryan Sarkisian; Yongming Deng; Kraig Wheeler; Hong Wang

doi:10.1055/s-0033-1338613

Oxa-diels-alder reaction of isatins and acyclic α,β-unsaturated methyl ketones through cooperative dienamine and metal lewis acid catalysis

Lu Liu
, Philias Daka
, Ryan Sarkisian
, Yongming Deng
, Kraig Wheeler
, Hong Wang^*

^*此作品的通讯作者

化学与分子工程学院

Miami University
Eastern Illinois University

科研成果: 期刊稿件 › 文章 › 同行评审

10 引用（Scopus）

摘要

Cooperative enamine and metal Lewis acid catalysis was applied to develop an asymmetric oxa-Diels-Alder reaction of isatins and but-3-en-2-ones. Spirooxindole tetrahydropyranones were obtained in good yields (58-86%), moderate stereoselectivities (1.3:1-5.9:1 dr, 50-81% ee), and excellent chemoselectivity.

源语言	英语
文章编号	SS-2014-C0028-OP
页（从-至）	1339-1347
页数	9
期刊	Synthesis (Germany)
卷	46
期	10
DOI	https://doi.org/10.1055/s-0033-1338613
出版状态	已出版 - 5月 2014

访问文件

10.1055/s-0033-1338613

其它文件与链接

链接到 Scopus 的出版物

引用此

@article{bfdbd4dc6a1a49f487923dcc817e05e6,

title = "Oxa-diels-alder reaction of isatins and acyclic α,β-unsaturated methyl ketones through cooperative dienamine and metal lewis acid catalysis",

abstract = "Cooperative enamine and metal Lewis acid catalysis was applied to develop an asymmetric oxa-Diels-Alder reaction of isatins and but-3-en-2-ones. Spirooxindole tetrahydropyranones were obtained in good yields (58-86\%), moderate stereoselectivities (1.3:1-5.9:1 dr, 50-81\% ee), and excellent chemoselectivity.",

keywords = "bifunctional catalysis, oxa-Diels-Alder reaction, spirooxindoles, tandem reactions, tetrahydropyranones",

author = "Lu Liu and Philias Daka and Ryan Sarkisian and Yongming Deng and Kraig Wheeler and Hong Wang",

year = "2014",

month = may,

doi = "10.1055/s-0033-1338613",

language = "英语",

volume = "46",

pages = "1339--1347",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "10",

}

TY - JOUR

T1 - Oxa-diels-alder reaction of isatins and acyclic α,β-unsaturated methyl ketones through cooperative dienamine and metal lewis acid catalysis

AU - Liu, Lu

AU - Daka, Philias

AU - Sarkisian, Ryan

AU - Deng, Yongming

AU - Wheeler, Kraig

AU - Wang, Hong

PY - 2014/5

Y1 - 2014/5

N2 - Cooperative enamine and metal Lewis acid catalysis was applied to develop an asymmetric oxa-Diels-Alder reaction of isatins and but-3-en-2-ones. Spirooxindole tetrahydropyranones were obtained in good yields (58-86%), moderate stereoselectivities (1.3:1-5.9:1 dr, 50-81% ee), and excellent chemoselectivity.

AB - Cooperative enamine and metal Lewis acid catalysis was applied to develop an asymmetric oxa-Diels-Alder reaction of isatins and but-3-en-2-ones. Spirooxindole tetrahydropyranones were obtained in good yields (58-86%), moderate stereoselectivities (1.3:1-5.9:1 dr, 50-81% ee), and excellent chemoselectivity.

KW - bifunctional catalysis

KW - oxa-Diels-Alder reaction

KW - spirooxindoles

KW - tandem reactions

KW - tetrahydropyranones

UR - https://www.scopus.com/pages/publications/84900481500

U2 - 10.1055/s-0033-1338613

DO - 10.1055/s-0033-1338613

M3 - 文章

AN - SCOPUS:84900481500

SN - 0039-7881

VL - 46

SP - 1339

EP - 1347

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 10

M1 - SS-2014-C0028-OP

ER -

Oxa-diels-alder reaction of isatins and acyclic α,β-unsaturated methyl ketones through cooperative dienamine and metal lewis acid catalysis

摘要

访问文件

其它文件与链接

学术指纹

引用此