Palladium-catalyzed three-component tandem cyclization reaction of 2-(2,3-allenyl)acylacetates, organic halides, and amines: An effective protocol for the synthesis of 4,5-dihydro-1H-pyrrole derivatives

Jiajia Cheng; Xuefeng Jiang; Can Zhu; Shengming Ma

doi:10.1002/adsc.201100002

Palladium-catalyzed three-component tandem cyclization reaction of 2-(2,3-allenyl)acylacetates, organic halides, and amines: An effective protocol for the synthesis of 4,5-dihydro-1H-pyrrole derivatives

Jiajia Cheng
, Xuefeng Jiang
, Can Zhu
, Shengming Ma^*

^*Corresponding author for this work

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

29 Scopus citations

Abstract

A domino three-component reaction of 2-(2′,3′-allenyl) acylacetates with aryl or alkenyl halides and aryl- or benzylamines afforded 4,5-dihydro-1H-pyrrole derivatives highly chemo- and regioselectively in one pot through imine formation/imine-enamine tautomerization under the catalysis of palladium(0) and toluenesulfonic acid monohydrate. A high diastereoselectivity was observed.

Original language	English
Pages (from-to)	1676-1682
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	353
Issue number	10
DOIs	https://doi.org/10.1002/adsc.201100002
State	Published - Jul 2011
Externally published	Yes

Keywords

4,5-dihydro-1H-pyrroles
allenes
cyclization
three-component reactions

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10.1002/adsc.201100002

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title = "Palladium-catalyzed three-component tandem cyclization reaction of 2-(2,3-allenyl)acylacetates, organic halides, and amines: An effective protocol for the synthesis of 4,5-dihydro-1H-pyrrole derivatives",

abstract = "A domino three-component reaction of 2-(2′,3′-allenyl) acylacetates with aryl or alkenyl halides and aryl- or benzylamines afforded 4,5-dihydro-1H-pyrrole derivatives highly chemo- and regioselectively in one pot through imine formation/imine-enamine tautomerization under the catalysis of palladium(0) and toluenesulfonic acid monohydrate. A high diastereoselectivity was observed.",

keywords = "4,5-dihydro-1H-pyrroles, allenes, cyclization, three-component reactions",

author = "Jiajia Cheng and Xuefeng Jiang and Can Zhu and Shengming Ma",

year = "2011",

month = jul,

doi = "10.1002/adsc.201100002",

language = "英语",

volume = "353",

pages = "1676--1682",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

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}

Palladium-catalyzed three-component tandem cyclization reaction of 2-(2,3-allenyl)acylacetates, organic halides, and amines: An effective protocol for the synthesis of 4,5-dihydro-1H-pyrrole derivatives. / Cheng, Jiajia; Jiang, Xuefeng; Zhu, Can et al.
In: Advanced Synthesis and Catalysis, Vol. 353, No. 10, 07.2011, p. 1676-1682.

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

TY - JOUR

T1 - Palladium-catalyzed three-component tandem cyclization reaction of 2-(2,3-allenyl)acylacetates, organic halides, and amines

T2 - An effective protocol for the synthesis of 4,5-dihydro-1H-pyrrole derivatives

AU - Cheng, Jiajia

AU - Jiang, Xuefeng

AU - Zhu, Can

AU - Ma, Shengming

PY - 2011/7

Y1 - 2011/7

N2 - A domino three-component reaction of 2-(2′,3′-allenyl) acylacetates with aryl or alkenyl halides and aryl- or benzylamines afforded 4,5-dihydro-1H-pyrrole derivatives highly chemo- and regioselectively in one pot through imine formation/imine-enamine tautomerization under the catalysis of palladium(0) and toluenesulfonic acid monohydrate. A high diastereoselectivity was observed.

AB - A domino three-component reaction of 2-(2′,3′-allenyl) acylacetates with aryl or alkenyl halides and aryl- or benzylamines afforded 4,5-dihydro-1H-pyrrole derivatives highly chemo- and regioselectively in one pot through imine formation/imine-enamine tautomerization under the catalysis of palladium(0) and toluenesulfonic acid monohydrate. A high diastereoselectivity was observed.

KW - 4,5-dihydro-1H-pyrroles

KW - allenes

KW - cyclization

KW - three-component reactions

UR - https://www.scopus.com/pages/publications/79960464307

U2 - 10.1002/adsc.201100002

DO - 10.1002/adsc.201100002

M3 - 文章

AN - SCOPUS:79960464307

SN - 1615-4150

VL - 353

SP - 1676

EP - 1682

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 10

ER -

Palladium-catalyzed three-component tandem cyclization reaction of 2-(2,3-allenyl)acylacetates, organic halides, and amines: An effective protocol for the synthesis of 4,5-dihydro-1H-pyrrole derivatives

Abstract

Keywords

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