The Nazarov Cyclization

F. G. West; O. Scadeng; Yen-Ku Wu; R. J. Fradette; S. Joy

doi:10.1016/B978-0-08-097742-3.00519-X

The Nazarov Cyclization

F. G. West^*, O. Scadeng, Yen-Ku Wu, R. J. Fradette, S. Joy

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Chapter in Book/Report/Conference proceeding › Chapter › peer-review

47 Scopus citations

Abstract

Although well established as a reliable method for forming new cyclopentenone rings from acyclic precursors, the Nazarov reaction has been the subject of substantial recent work. The effect of substituents on 1,4-dien-3-one precursors is discussed. Asymmetric methods are presented, including chirality transfer, chiral Lewis acids, and asymmetric organocatalysis. An overview is given of various 'interrupted' variants, in which cyclized intermediates undergo domino trapping reactions with either nucleophilic or electrophilic reagents. Finally, cyclization via alternative and unconventional precursors is described, including the vinylogous and iso-Nazarov reactions, transition metal activation of alkyne-containing substrates, and the aza-Nazarov reaction.

Original language	English
Title of host publication	Comprehensive Organic Synthesis
Subtitle of host publication	Second Edition
Publisher	Elsevier Ltd
Pages	827-866
Number of pages	40
Volume	5
ISBN (Print)	9780080977430
DOIs	https://doi.org/10.1016/B978-0-08-097742-3.00519-X
State	Published - 1 Feb 2014

Keywords

Asymmetric
Catalysis
Cycloaddition
Cyclopentenone
Domino process
Electrocyclization
Metallo-Nazarov
Nazarov reaction
Piancatelli reaction

Access to Document

10.1016/B978-0-08-097742-3.00519-X

Fingerprint Dive into the research topics of 'The Nazarov Cyclization'. Together they form a unique fingerprint.

Cite this

@inbook{d9a81e3197234a558105727e71bc9193,

title = "The Nazarov Cyclization",

abstract = "Although well established as a reliable method for forming new cyclopentenone rings from acyclic precursors, the Nazarov reaction has been the subject of substantial recent work. The effect of substituents on 1,4-dien-3-one precursors is discussed. Asymmetric methods are presented, including chirality transfer, chiral Lewis acids, and asymmetric organocatalysis. An overview is given of various 'interrupted' variants, in which cyclized intermediates undergo domino trapping reactions with either nucleophilic or electrophilic reagents. Finally, cyclization via alternative and unconventional precursors is described, including the vinylogous and iso-Nazarov reactions, transition metal activation of alkyne-containing substrates, and the aza-Nazarov reaction.",

keywords = "Asymmetric, Catalysis, Cycloaddition, Cyclopentenone, Domino process, Electrocyclization, Metallo-Nazarov, Nazarov reaction, Piancatelli reaction",

author = "West, {F. G.} and O. Scadeng and Yen-Ku Wu and Fradette, {R. J.} and S. Joy",

year = "2014",

month = feb,

day = "1",

doi = "10.1016/B978-0-08-097742-3.00519-X",

language = "English",

isbn = "9780080977430",

volume = "5",

pages = "827--866",

booktitle = "Comprehensive Organic Synthesis",

publisher = "Elsevier Ltd",

address = "United Kingdom",

}

TY - CHAP

T1 - The Nazarov Cyclization

AU - West, F. G.

AU - Scadeng, O.

AU - Wu, Yen-Ku

AU - Fradette, R. J.

AU - Joy, S.

PY - 2014/2/1

Y1 - 2014/2/1

N2 - Although well established as a reliable method for forming new cyclopentenone rings from acyclic precursors, the Nazarov reaction has been the subject of substantial recent work. The effect of substituents on 1,4-dien-3-one precursors is discussed. Asymmetric methods are presented, including chirality transfer, chiral Lewis acids, and asymmetric organocatalysis. An overview is given of various 'interrupted' variants, in which cyclized intermediates undergo domino trapping reactions with either nucleophilic or electrophilic reagents. Finally, cyclization via alternative and unconventional precursors is described, including the vinylogous and iso-Nazarov reactions, transition metal activation of alkyne-containing substrates, and the aza-Nazarov reaction.

AB - Although well established as a reliable method for forming new cyclopentenone rings from acyclic precursors, the Nazarov reaction has been the subject of substantial recent work. The effect of substituents on 1,4-dien-3-one precursors is discussed. Asymmetric methods are presented, including chirality transfer, chiral Lewis acids, and asymmetric organocatalysis. An overview is given of various 'interrupted' variants, in which cyclized intermediates undergo domino trapping reactions with either nucleophilic or electrophilic reagents. Finally, cyclization via alternative and unconventional precursors is described, including the vinylogous and iso-Nazarov reactions, transition metal activation of alkyne-containing substrates, and the aza-Nazarov reaction.

KW - Asymmetric

KW - Catalysis

KW - Cycloaddition

KW - Cyclopentenone

KW - Domino process

KW - Electrocyclization

KW - Metallo-Nazarov

KW - Nazarov reaction

KW - Piancatelli reaction

UR - http://www.scopus.com/inward/record.url?scp=84899633670&partnerID=8YFLogxK

U2 - 10.1016/B978-0-08-097742-3.00519-X

DO - 10.1016/B978-0-08-097742-3.00519-X

M3 - Chapter

AN - SCOPUS:84899633670

SN - 9780080977430

VL - 5

SP - 827

EP - 866

BT - Comprehensive Organic Synthesis

PB - Elsevier Ltd

ER -

The Nazarov Cyclization

Abstract

Keywords

Access to Document

Other files and links

Cite this