Ring‐Expansion Approach to Medium‐Sized Lactams and Analysis of Their Medicinal Lead‐Like Properties DOI

Laetitia G. Baud,

Morgan A. Manning,

Helen L. Arkless

et al.

Chemistry - A European Journal, Journal Year: 2016, Volume and Issue: 23(9), P. 2225 - 2230

Published: Dec. 9, 2016

Medium-sized rings are widely considered to be under-represented in biological screening libraries for lead identification medicinal chemistry. To help address this, a library of medium-sized lactams has been generated by using simple, scalable and versatile ring-expansion protocol. Analysis the open-access computational tool LLAMA suggested that these their derivatives have highly promising physicochemical 3D spatial properties thus much potential drug discovery.

Language: Английский

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions DOI
Qiang Cheng, Hang‐Fei Tu, Chao Zheng

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 119(3), P. 1855 - 1969

Published: Dec. 24, 2018

In this review, we summarize the origin and advancements of iridium-catalyzed asymmetric allylic substitution reactions during past two decades. Since first report in 1997, Ir-catalyzed have attracted intense attention due to their exceptionally high regio- enantioselectivities. been significantly developed recent years many respects, including ligand development, mechanistic understanding, substrate scope, application synthesis complex functional molecules. an explicit outline ligands, mechanism, scope nucleophiles, applications is presented.

Language: Английский

Citations

674

Catalytic Asymmetric Dearomatization by Transition-Metal Catalysis: A Method for Transformations of Aromatic Compounds DOI Creative Commons
Chao Zheng, Shu‐Li You

Chem, Journal Year: 2016, Volume and Issue: 1(6), P. 830 - 857

Published: Dec. 1, 2016

Language: Английский

Citations

507

Construction of Nine‐Membered Heterocycles through Palladium‐Catalyzed Formal [5+4] Cycloaddition DOI
Li‐Cheng Yang, Zi‐Qiang Rong, Ya‐Nong Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 56(11), P. 2927 - 2931

Published: Feb. 6, 2017

Abstract The first catalytic formal [5+4] cycloaddition to prepare nine‐membered heterocycles is presented. Under palladium catalysis, the reaction of N‐tosyl azadienes and substituted vinylethylene carbonates (VECs) proceeds smoothly produce benzofuran‐fused in uniformly high efficiency. Highly diastereoselective functionalization through peripheral attack also demonstrated.

Language: Английский

Citations

264

Recent progress in transition-metal-catalyzed enantioselective indole functionalizations DOI
Jing-Biao Chen, Yi‐Xia Jia

Organic & Biomolecular Chemistry, Journal Year: 2017, Volume and Issue: 15(17), P. 3550 - 3567

Published: Jan. 1, 2017

Numerous efficient synthetic methods for enantioselective indole functionalizations have emerged in recent years. This review summarizes the major achievements transition-metal-catalyzed functionalization reactions since 2010 and focuses on C-C bond formation processes, including alkylations, arylations, cycloaddition reactions, other reactions. It intends to give a compendious overview of significant progress achieved this area.

Language: Английский

Citations

256

Nine-Membered Benzofuran-Fused Heterocycles: Enantioselective Synthesis by Pd-Catalysis and Rearrangement via Transannular Bond Formation DOI
Zi‐Qiang Rong, Li‐Cheng Yang, Song Liu

et al.

Journal of the American Chemical Society, Journal Year: 2017, Volume and Issue: 139(43), P. 15304 - 15307

Published: Oct. 17, 2017

The first enantioselective formal [5+4] cycloaddition is realized under palladium catalysis to deliver benzofuran-fused nine-membered rings. These medium-sized heterocycles and derivatives undergo unique rearrangements induced by transannular bond formation, resulting in the production of two classes densely substituted polycyclic excellent efficiency stereoselectivity.

Language: Английский

Citations

238

Ring‐Expansion Reactions in the Synthesis of Macrocycles and Medium‐Sized Rings DOI

James R. Donald,

William P. Unsworth

Chemistry - A European Journal, Journal Year: 2017, Volume and Issue: 23(37), P. 8780 - 8799

Published: March 15, 2017

Functionalised macrocycles and medium-sized rings have applications in a number of scientific fields, ranging from medicinal chemistry supramolecular chemistry, to catalysis nanotechnology. However, their value these areas can be undermined by simple, but important limitation: large ring systems are very often difficult make. Traditional end-to-end cyclisation reactions long linear precursors typically unpredictable impractical processes, mainly due unfavourable enthalpic entropic factors. Most published methods make focus on minimising the damage inflicted performing step; contrast, ring-expansion enable it avoided altogether. In this Review article, is highlighted how "growing" existing cyclic via expansion expedite efficient, practical scalable synthesis rings.

Language: Английский

Citations

235

Highly Enantioselective [5 + 2] Annulations through Cooperative N-Heterocyclic Carbene (NHC) Organocatalysis and Palladium Catalysis DOI
Santanu Singha, Tuhin Patra, Constantin G. Daniliuc

et al.

Journal of the American Chemical Society, Journal Year: 2018, Volume and Issue: 140(10), P. 3551 - 3554

Published: Feb. 22, 2018

The highly enantioselective [5 + 2] annulation of enals with vinylethylene carbonates through a cooperative N-heterocyclic carbene (NHC)/Pd catalytic system is reported. use bidentate phosphine ligand was crucial to prevent coordination the NHC organocatalyst active Pd catalyst. complementary and matched combination chiral catalyst promotes high levels both reactivity enantioselectivity (mostly ≥99% ee).

Language: Английский

Citations

233

Chiral Monophosphorus Ligands for Asymmetric Catalytic Reactions DOI
Wen‐Zhen Fu, Wenjun Tang

ACS Catalysis, Journal Year: 2016, Volume and Issue: 6(8), P. 4814 - 4858

Published: June 9, 2016

Chiral monophosphorus ligands are playing an important role for the recent advances in asymmetric catalysis. This review summarizes latest progress various catalytic reactions with employment of chiral including allylic substitution, dearomative arylation, Heck reaction, cross-coupling, C–H bond functionalization, coupling π systems, addition, hydrogenation, and organocatalytic reactions. The new reactivity, selectivity, reaction mechanism enabled by these discussed.

Language: Английский

Citations

230

Pd‐Catalyzed Enantioselective [6+4] Cycloaddition of Vinyl Oxetanes with Azadienes to Access Ten‐Membered Heterocycles DOI
Ya‐Nong Wang, Li‐Cheng Yang, Zi‐Qiang Rong

et al.

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 57(6), P. 1596 - 1600

Published: Dec. 19, 2017

Abstract We report herein the first enantioselective cycloaddition of vinyl oxetanes, reaction which with azadienes provided unprecedented access to ten‐membered heterocycles through a [6+4] cycloaddition. By using commercially available chiral Pd‐SIPHOX catalyst, wide range benzofuran‐ as well indole‐fused could be accessed in excellent yield and enantioselectivity. A unique Lewis acid induced fragmentation these was also discovered.

Language: Английский

Citations

174

Catalytic Asymmetric Umpolung Allylation of Imines DOI
Jie Liu, Chao-Guo Cao, Hongbao Sun

et al.

Journal of the American Chemical Society, Journal Year: 2016, Volume and Issue: 138(40), P. 13103 - 13106

Published: Sept. 19, 2016

Here we report an iridium-catalyzed asymmetric umpolung allylation of imines as a general approach to prepare 1,4-disubstituted homoallylic amines, fundamental class compounds that are hitherto not straightforward obtain. This transformation proceeds by cascade involving intermolecular regioselective 2-azaallyl anions and following 2-aza-Cope rearrangement, utilizes easily available reagents catalysts, tolerates substantial scope substrates, readily leads various enantioenriched, primary amines.

Language: Английский

Citations

149