Exploring bis-(amino)cyclopropenylidene as a non-covalent Brønsted base catalyst in conjugate addition reactions

2018 ◽  
Vol 16 (3) ◽  
pp. 384-388 ◽  
Author(s):  
Gurdeep Singh ◽  
Prithwish Goswami ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Base Catalyst ◽  
Quinone Methides ◽  
Carbon Nucleophiles ◽  
Catalytic Application ◽  
Brønsted Base

The catalytic application of bis-(amino)cyclopropenylidene, as a non-covalent Brønsted base, in the 1,4- and 1,6-conjugate addition of carbon nucleophiles to enones andp-quinone methides, respectively, is described.

Expedient access to unsymmetrical triarylmethanes through N-heterocyclic carbene catalysed 1,6-conjugate addition of 2-naphthols to para-quinone methides

RSC Advances ◽  
2016 ◽  
Vol 6 (81) ◽  
pp. 77111-77115 ◽  
Author(s):  
Panjab Arde ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Conjugate Addition ◽  
Base Catalyst ◽  
Quinone Methides ◽  
Brønsted Base

A direct and atom-economical protocol for the synthesis of unsymmetrical triarylmethanes through 1,6-conjugate addition of 2-naphthols topara-quinone methides using N-heterocyclic carbene as a Brønsted base catalyst is described.

scholarly journals Cover Feature: para -Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules (Eur. J. Org. Chem. 18/2020)

2020 ◽  
Vol 2020 (18) ◽  
pp. 2642-2642
Author(s):  
Carolina G. S. Lima ◽  
Fernanda P. Pauli ◽  
Dora C. S. Costa ◽  
Acácio S. de Souza ◽  
Luana S. M. Forezi ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Quinone Methides

ChemInform Abstract: Conjugate Addition Reactions of Carbon Nucleophiles to Electron-Deficient Dienes.

ChemInform ◽  
2011 ◽  
Vol 42 (7) ◽  
pp. no-no
Author(s):  
Aurelio G. Csaky ◽  
Gabriela de la Herran ◽  
M. Carmen Murcia
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Carbon Nucleophiles ◽  
Electron Deficient Dienes

N-Heterocyclic carbene catalysed 1,6-hydrophosphonylation of p-quinone methides and fuchsones: an atom economical route to unsymmetrical diaryl- and triarylmethyl phosphonates

2016 ◽  
Vol 14 (24) ◽  
pp. 5550-5554 ◽  
Author(s):  
Panjab Arde ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Direct Method ◽  
Base Catalyst ◽  
Quinone Methides ◽  
Brønsted Base ◽  
A Direct Method

A direct method for the synthesis of diaryl- and triarylmethyl phosphonates through 1,6-hydrophosphonylation ofp-quinone methides and fuchsones using NHC as a Brønsted base catalyst is described.

para -Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules

2020 ◽  
Vol 2020 (18) ◽  
pp. 2650-2692 ◽  
Author(s):  
Carolina G. S. Lima ◽  
Fernanda P. Pauli ◽  
Dora C. S. Costa ◽  
Acácio S. de Souza ◽  
Luana S. M. Forezi ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Quinone Methides

Organocatalytic Asymmetric Tandem Conjugate Addition–Protonation of Azlactones to N-Itaconimides

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1310-1314 ◽  
Author(s):  
Xiaowei Zhao ◽  
Zhiyong Jiang ◽  
Gao Zhang ◽  
Yanli Yin
Keyword(s):  
Tertiary Amine ◽  
Conjugate Addition ◽  
Base Catalyst ◽  
Asymmetric Reaction ◽  
Efficient Approach ◽  
Brønsted Base ◽  
Catalytic Asymmetric

An unprecedented catalytic asymmetric reaction between azlactones and N-itaconimides has been developed. In the presence of an l-tert-leucine-based urea–tertiary amine Brønsted base catalyst, the tandem conjugate addition–protonation products could be attained in moderate yields with excellent enantio- and diastereoselectivities (up to 99% ee and >20:1 dr). The method provides an efficient approach to access valuable chiral γ-tertiary amine substituted succinimides containing nonadjacent stereocenters.

Stereoselective Reactions of ortho-Quinone Methide and ortho-Quinone Methide Imines and Their Utility in Natural Product Synthesis

Synthesis ◽  
2018 ◽  
Vol 50 (20) ◽  
pp. 4008-4018 ◽  
Author(s):  
Alan Spivey ◽  
Christian Nielsen ◽  
Hossay Abas
Keyword(s):  
Total Synthesis ◽  
Conjugate Addition ◽  
Natural Product Synthesis ◽  
Quinone Methide ◽  
Addition Reactions ◽  
Quinone Methides ◽  
New Methods ◽  
Synthetic Utility ◽  
Stereoselective Reactions ◽  
Significant Attention

Herein presented is a review of the reactivity and synthetic utility of ortho-quinone methides and ortho-quinone methide imines. These versatile intermediates have received significant attention in the literature and new methods for their preparation and reaction as well as recent applications in total synthesis are discussed.1 Introduction2 Conjugate Addition Reactions3 Concerted Cycloaddition Reactions4 Stepwise Addition Reactions5 Applications in Total Synthesis6 Conclusion

Recent developments in 1,6-addition reactions of para-quinone methides (p-QMs)

2020 ◽  
Vol 7 (13) ◽  
pp. 1743-1778 ◽  
Author(s):  
Jia-Yin Wang ◽  
Wen-Juan Hao ◽  
Shu-Jiang Tu ◽  
Bo Jiang
Keyword(s):  
Recent Progress ◽  
Conjugate Addition ◽  
Addition Reactions ◽  
Quinone Methides ◽  
Comprehensive Overview ◽  
Recent Developments

In this review, we provide a comprehensive overview of recent progress in this rapidly growing field by summarizing the 1,6-conjugate addition and annulation reactions of p-QMs with consideration of their mechanisms and applications.

scholarly journals Programmed Sequential Additions to Halogenated Mucononitriles

2020 ◽  
Author(s):  
Adam Zahara ◽  
Elsa Hinds ◽  
Andrew Nguyen ◽  
Sidney Wilkerson-Hill
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Conjugate Addition ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Carbon Nucleophiles ◽  
Multicomponent Coupling

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

scholarly journals Programmed Sequential Additions to Halogenated Mucononitriles

2020 ◽  
Author(s):  
Adam Zahara ◽  
Elsa Hinds ◽  
Andrew Nguyen ◽  
Sidney Wilkerson-Hill
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Conjugate Addition ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Carbon Nucleophiles ◽  
Multicomponent Coupling

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

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