Tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine

Yeong Jiunn Jang; Siang En Syu; Yi Wun Jhang; Yu Ting Lee; Chia Jui Lee; Ko Wei Chen; Utpal Das; Wenwei Lin

doi:10.3390/molecules17032529

Tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine

Yeong Jiunn Jang, Siang En Syu, Yi Wun Jhang, Yu Ting Lee, Chia Jui Lee, Ko Wei Chen, Utpal Das, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

2 Citations (Scopus)

Abstract

A new highly efficient three-component reaction of alkyl acrylate, aldehyde and dialkyl malonate using ethyl diphenylphosphine as organocatalyst has been described. Various highly functional compounds bearing hydroxyl groups and the ester functions can be easily prepared in moderate to good yields according to our one-step procedure. The reactions are believed to proceed via Morita-Baylis-Hillman reactions of alkyl acrylate and aldehydes, followed by the Michael addition reactions of dialkyl malonates. Our reactions indicated that the intermediate species formed in the phosphine-catalyzed MBH reaction are an effective organic base to catalyze the Michael addition reactions of dialkyl malonates to the preformed MBH adducts.

Original language	English
Pages (from-to)	2529-2541
Number of pages	13
Journal	Molecules
Volume	17
Issue number	3
DOIs	https://doi.org/10.3390/molecules17032529
Publication status	Published - 2012 Mar

Keywords

Aldehyde
Chemoselectivity
Michael addition
Morita-Baylis-Hillman
Multicomponent reaction

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.3390/molecules17032529

Cite this

@article{519ccb175ef04bffb84c2ccc2c6e598f,

title = "Tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine",

abstract = "A new highly efficient three-component reaction of alkyl acrylate, aldehyde and dialkyl malonate using ethyl diphenylphosphine as organocatalyst has been described. Various highly functional compounds bearing hydroxyl groups and the ester functions can be easily prepared in moderate to good yields according to our one-step procedure. The reactions are believed to proceed via Morita-Baylis-Hillman reactions of alkyl acrylate and aldehydes, followed by the Michael addition reactions of dialkyl malonates. Our reactions indicated that the intermediate species formed in the phosphine-catalyzed MBH reaction are an effective organic base to catalyze the Michael addition reactions of dialkyl malonates to the preformed MBH adducts.",

keywords = "Aldehyde, Chemoselectivity, Michael addition, Morita-Baylis-Hillman, Multicomponent reaction",

author = "Jang, {Yeong Jiunn} and Syu, {Siang En} and Jhang, {Yi Wun} and Lee, {Yu Ting} and Lee, {Chia Jui} and Chen, {Ko Wei} and Utpal Das and Wenwei Lin",

year = "2012",

month = mar,

doi = "10.3390/molecules17032529",

language = "English",

volume = "17",

pages = "2529--2541",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "3",

}

TY - JOUR

T1 - Tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine

AU - Jang, Yeong Jiunn

AU - Syu, Siang En

AU - Jhang, Yi Wun

AU - Lee, Yu Ting

AU - Lee, Chia Jui

AU - Chen, Ko Wei

AU - Das, Utpal

AU - Lin, Wenwei

PY - 2012/3

Y1 - 2012/3

N2 - A new highly efficient three-component reaction of alkyl acrylate, aldehyde and dialkyl malonate using ethyl diphenylphosphine as organocatalyst has been described. Various highly functional compounds bearing hydroxyl groups and the ester functions can be easily prepared in moderate to good yields according to our one-step procedure. The reactions are believed to proceed via Morita-Baylis-Hillman reactions of alkyl acrylate and aldehydes, followed by the Michael addition reactions of dialkyl malonates. Our reactions indicated that the intermediate species formed in the phosphine-catalyzed MBH reaction are an effective organic base to catalyze the Michael addition reactions of dialkyl malonates to the preformed MBH adducts.

AB - A new highly efficient three-component reaction of alkyl acrylate, aldehyde and dialkyl malonate using ethyl diphenylphosphine as organocatalyst has been described. Various highly functional compounds bearing hydroxyl groups and the ester functions can be easily prepared in moderate to good yields according to our one-step procedure. The reactions are believed to proceed via Morita-Baylis-Hillman reactions of alkyl acrylate and aldehydes, followed by the Michael addition reactions of dialkyl malonates. Our reactions indicated that the intermediate species formed in the phosphine-catalyzed MBH reaction are an effective organic base to catalyze the Michael addition reactions of dialkyl malonates to the preformed MBH adducts.

KW - Aldehyde

KW - Chemoselectivity

KW - Michael addition

KW - Morita-Baylis-Hillman

KW - Multicomponent reaction

UR - http://www.scopus.com/inward/record.url?scp=84858987271&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84858987271&partnerID=8YFLogxK

U2 - 10.3390/molecules17032529

DO - 10.3390/molecules17032529

M3 - Article

C2 - 22446986

AN - SCOPUS:84858987271

SN - 1420-3049

VL - 17

SP - 2529

EP - 2541

JO - Molecules

JF - Molecules

IS - 3

ER -

Tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this