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^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

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.

Original language	English
Article number	SS-2014-C0028-OP
Pages (from-to)	1339-1347
Number of pages	9
Journal	Synthesis (Germany)
Volume	46
Issue number	10
DOIs	https://doi.org/10.1055/s-0033-1338613
State	Published - May 2014

Keywords

bifunctional catalysis
oxa-Diels-Alder reaction
spirooxindoles
tandem reactions
tetrahydropyranones

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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)",

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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

Abstract

Keywords

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