Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes

De Wei Wang; Siang En Syu; Yi Ting Hung; Pei Yi Chen; Chia Jui Lee; Ko Wei Chen; Yu Jhang Chen; Wenwei Lin

doi:10.1039/c0ob00644k

Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes

De Wei Wang
, Siang En Syu
, Yi Ting Hung
, Pei Yi Chen
, Chia Jui Lee
, Ko Wei Chen
, Yu Jhang Chen
, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

10 Citations (Scopus)

Abstract

An EtPPh₂- or PPh₃-catalyzed tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide is developed. Its further application in one-pot syntheses of highly functional alkenes starting from aldehydes, alkyl vinyl ketones, and amides is realized. A wide variety of highly functional α,β-unsaturated ketones can be furnished in 68-99% yields with high stereoselectivity (E/Z up to 98:2) within overall 3-29.5 h.

Original language	English
Pages (from-to)	363-366
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	2
DOIs	https://doi.org/10.1039/c0ob00644k
Publication status	Published - 2011 Jan 21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c0ob00644k

Cite this

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title = "Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes",

abstract = "An EtPPh2- or PPh3-catalyzed tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide is developed. Its further application in one-pot syntheses of highly functional alkenes starting from aldehydes, alkyl vinyl ketones, and amides is realized. A wide variety of highly functional α,β-unsaturated ketones can be furnished in 68-99\% yields with high stereoselectivity (E/Z up to 98:2) within overall 3-29.5 h.",

author = "Wang, \{De Wei\} and Syu, \{Siang En\} and Hung, \{Yi Ting\} and Chen, \{Pei Yi\} and Lee, \{Chia Jui\} and Chen, \{Ko Wei\} and Chen, \{Yu Jhang\} and Wenwei Lin",

year = "2011",

month = jan,

day = "21",

doi = "10.1039/c0ob00644k",

language = "English",

volume = "9",

pages = "363--366",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "2",

}

TY - JOUR

T1 - Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide

T2 - One-pot syntheses of highly functional alkenes

AU - Wang, De Wei

AU - Syu, Siang En

AU - Hung, Yi Ting

AU - Chen, Pei Yi

AU - Lee, Chia Jui

AU - Chen, Ko Wei

AU - Chen, Yu Jhang

AU - Lin, Wenwei

PY - 2011/1/21

Y1 - 2011/1/21

N2 - An EtPPh2- or PPh3-catalyzed tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide is developed. Its further application in one-pot syntheses of highly functional alkenes starting from aldehydes, alkyl vinyl ketones, and amides is realized. A wide variety of highly functional α,β-unsaturated ketones can be furnished in 68-99% yields with high stereoselectivity (E/Z up to 98:2) within overall 3-29.5 h.

AB - An EtPPh2- or PPh3-catalyzed tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide is developed. Its further application in one-pot syntheses of highly functional alkenes starting from aldehydes, alkyl vinyl ketones, and amides is realized. A wide variety of highly functional α,β-unsaturated ketones can be furnished in 68-99% yields with high stereoselectivity (E/Z up to 98:2) within overall 3-29.5 h.

UR - https://www.scopus.com/pages/publications/78650754320

UR - https://www.scopus.com/pages/publications/78650754320#tab=citedBy

U2 - 10.1039/c0ob00644k

DO - 10.1039/c0ob00644k

M3 - Article

AN - SCOPUS:78650754320

SN - 1477-0520

VL - 9

SP - 363

EP - 366

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 2

ER -

Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes

Abstract

ASJC Scopus subject areas

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CCDC 775300: Experimental Crystal Structure Determination

CCDC 770519: Experimental Crystal Structure Determination

CCDC 778974: Experimental Crystal Structure Determination

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Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

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Datasets

CCDC 775300: Experimental Crystal Structure Determination

CCDC 770519: Experimental Crystal Structure Determination

CCDC 778974: Experimental Crystal Structure Determination

Cite this