Domino Reactions with Dicyanoalkenes and Fluorinated Conjugated Sulfinyl Imines. A Convenient Strategy for the Generation of Structural Diversity DOI Creative Commons
Daniel Gaviña, Marcos Escolano, Lia Sotorríos

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(4), P. 970 - 981

Published: Nov. 13, 2023

Abstract Dicyanoalkenes are versatile reagents in organic synthesis and they have been extensively used a wide variety of transformations. However, their reactivity towards fluorinated imines remained almost unnoticed. The divergent conjugated sulfinyl with dicyanoalkenes is described herein. On the one hand, when tert ‐butyl were employed, cycloaromatization cascade process took place preferentially, rendering valuable trifluoromethyl arenes. other reaction p ‐tolyl mainly led to complex tetracyclic skeleton, involving an azetidinimine rearrangement intermediate. Finally, 1‐indanone‐derived aromatization was interrupted, new family diene derivatives. Theoretical calculations performed order shed light on mechanistic outcome this transformation.

Language: Английский

Synthesis of Chiral Heterocycles Through Enantioselective Silver‐Catalyzed Transformations DOI Open Access

Hélène Pellissier

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Abstract This review collects the recent developments in synthesis of chiral heterocycles through enantioselective silver‐catalyzed transformations published since 2018. It demonstrates power silver catalysts as special mild Lewis acids to provide an impressive diversity reaction pathways, such 1,3‐dipolar cycloadditions, various types cyclizations, along with a wide variety more complex domino/tandem reactions, allowing many novel heterocyclic products be achieved high enantioselectivities.

Language: Английский

Citations

1

Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis DOI Creative Commons
Heng Wang,

Xiaofeng Jie,

Qinglei Chong

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: April 23, 2024

Catalytic cascade transformations of simple starting materials into highly functionalized molecules bearing a stereochemically defined multisubstituted alkene, which are important in medicinal chemistry, natural product synthesis, and material science, high demand for organic synthesis. The development multiple reaction pathways accurately controlled by catalysts derived from different ligands is critical goal the field catalysis. Here we report cobalt-catalyzed strategy direct coupling inexpensive 1,3-enynes with two acrylates to construct diversity 1,3-dienes containing trisubstituted or tetrasubstituted olefin. Such reactions can proceed through three initiated oxidative cyclization achieve bond formation chemo-, regio- stereoselectivity precisely ligands, providing platform tandem carbon-carbon bond-forming reactions.

Language: Английский

Citations

7

Catalytic enantioselective alkenylation–heteroarylation of olefins: stereoselective syntheses of 5–7 membered azacycles and oxacycles DOI Creative Commons

Zhaoming Ma,

Lantian Sun,

Jianrong Steve Zhou

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(11), P. 3010 - 3017

Published: Jan. 1, 2023

Catalytic enantioselective domino alkenylation-heteroarylation of nonconjugated iododienes proceeded with excellent stereoselectivity and broad scope substrates. The reaction enables stereoselective syntheses substituted azacycles such as piperidine, pyrrolidine azepine dihydropyrans carrying new quaternary stereocenters. Mechanistically, C-H bonds heterocycles were activated by lithium alkoxides via reversible deprotonation, rather than conventional palladium(ii)-assisted metalation processes. Many types heteroarenes can be used, including not only azoles (such thiazoles, oxazoles, imidazoles oxadiazoles), but also nonazoles (thiophene, furan azine N-oxides).

Language: Английский

Citations

10

Asymmetric cascades of the π-allyl complex: a journey from transition-metal catalysis to metallaphotocatalysis DOI
Santosh K. Nanda

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(76), P. 11298 - 11319

Published: Jan. 1, 2023

The enantioselective catalytic cascade involving Tsuji-Trost allylation has provided a viable strategy for the construction of multiple asymmetric C-C and C-X centres numerous methods have been developed around it synthesis various vital scaffolds. synthetic utility this was enhanced by replacing customary allyl acetates with ethylene diacetates/dicarbonates, vinyl epoxides, oxetanes, carbonates, cyclopropanes, enynes, dienes using transition-metal catalysis. One more milestone achieved when metallaphotocatalysis necessary platform these cascades cheaper metal. This review will provide summary from 2015.

Language: Английский

Citations

10

Recent Developments in Asymmetric Nazarov Reactions DOI

Hélène Pellissier

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(10), P. 757 - 776

Published: April 17, 2024

Abstract: The Nazarov reaction involves the cyclization of divinyl ketones into cyclopentenones under influence strong acids. prevalence five-membered carbocycles in a multitude natural and bioactive products has triggered an intense development efficient methods for their construction. In particular, asymmetric versions are achieved by using either chiral auxiliary or catalyst, which can be organocatalyst, metal multicatalytic system. This review aims to update field reactions published since 2017. It is divided four sections, dealing successively with auxiliaries, organocatalytic enantioselective reactions, metal/boron-catalyzed reactions. Each section subdivided simple Nazarov-based domino/tandem have allowed numerous more complex functionalized molecules synthesized one-pot procedures.

Language: Английский

Citations

4

Recent Developments in Enantioselective Silver-Catalyzed Transformations DOI

Hélène Pellissier

Organic Preparations and Procedures International, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 95

Published: April 11, 2025

Language: Английский

Citations

0

Catalytic enantioselective domino alkenylation-alkynylation of alkenes: stereoselective synthesis of 5–7 membered azacycles and carbocycles DOI

Zhaoming Ma,

Lantian Sun,

Jianrong Steve Zhou

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(6), P. 1701 - 1706

Published: April 10, 2023

Language: Английский

Citations

7

Recent developments in enantioselective nickel-catalysed cycloadditions DOI

Hélène Pellissier

Tetrahedron, Journal Year: 2024, Volume and Issue: 153, P. 133840 - 133840

Published: Jan. 20, 2024

Language: Английский

Citations

2

Enantioselective iron-catalysed transformations. An update DOI

Hélène Pellissier

Tetrahedron, Journal Year: 2024, Volume and Issue: 157, P. 133944 - 133944

Published: March 23, 2024

Language: Английский

Citations

1

Asymmetric organocatalytic Morita−Baylis−Hillman reaction and asymmetric organocatalytic transformations of Morita−Baylis−Hillman adducts. An update DOI

Hélène Pellissier

Tetrahedron, Journal Year: 2024, Volume and Issue: 172, P. 134435 - 134435

Published: Dec. 23, 2024

Language: Английский

Citations

1