<i>N</i>-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines

Wang, Ming; Huang, Zhijian; Xu, Jianfeng; Robin, Yonggui

doi:10.1021/ja411110f

Cited by 235 publications

(73 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The nucleophilic γ activation of α,β‐unsaturated aldehyde 43 through an NHC‐catalyzed oxidative process was introduced by Chi and co‐workers in 2012 . They also utilized this strategy in the enantioselective KR of azomethine imines 44 (Scheme ) . Azomethine imines 44 are important building blocks in the construction of biologically active dinitrogen‐fused heterocyclic compounds.…”

Section: Kinetic Resolutions In Nhc Organocatalysismentioning

confidence: 99%

N‐Heterocyclic Carbene (NHC)‐Organocatalyzed Kinetic Resolutions, Dynamic Kinetic Resolutions, and Desymmetrizations

Wang

Pan

et al. 2018

Chemistry An Asian Journal

View full text Add to dashboard Cite

The last couple of decades have witnessed tremendous development within N-heterocyclic carbene (NHC) organocatalysis. NHCs have been used as powerful organic catalysts in asymmetric synthesis. Although great achievements have been made in asymmetric NHC catalysis, their applications in kinetic resolution (KR), dynamic kinetic resolution (DKR), and desymmetrization processes have been relatively less developed. Moreover, limited activation modes have been involved in these processes. This review provides an overview of the NHC-organocatalyzed KR, DKR, and desymmetrization reactions in the preparation of chiral functional molecules. The aim is to highlight both the importance and elegance of these methods in the construction of challenging chiral compounds and to provide our own perspective on future development in this direction.

show abstract

Section: Kinetic Resolutions In Nhc Organocatalysismentioning

confidence: 99%

N‐Heterocyclic Carbene (NHC)‐Organocatalyzed Kinetic Resolutions, Dynamic Kinetic Resolutions, and Desymmetrizations

Wang

Pan

et al. 2018

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

“…In 2014, the Chi group developed an NHC‐catalyzed [3+4] cycloaddition reaction for the kinetic resolution of azomethine imines (Scheme ) . The vinyl enolate, which was afforded through oxidative γ‐carbon activation of an enal, was employed as the reactive 1,4‐dipolarophile.…”

Section: Kinetic Resolution Of Amines and Iminesmentioning

confidence: 99%

Recent Progress in (Dynamic) Kinetic Resolution Catalyzed by N‐Heterocyclic Carbenes

Chen

Shi²,

Wang

2018

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

Catalytic kinetic resolution is often the "method of choice" for the preparation of optically enriched functionalized compounds and, over the past decade, kinetic resolutions and dynamic kinetic resolutions catalyzed by N-heterocyclic carbenes (NHCs) have been employed for the synthesis of a variety of optically enriched functionalized molecules. Herein we provide an overview of reported NHC-catalyzed kinetic resolutions in terms of the structure of the substrate, the reaction type, and the activation mode. This Focus Review is arranged according to the structure of the racemic compounds and includes the kinetic resolution of alcohols, amines, imines, and aldehydes, as well as dynamic kinetic resolution. In each section, the activation mode and reaction mechanism are discussed. We conclude with a summary of the current state-of-play in NHC-catalyzed kinetic resolution and provide an outlook for the development of this field in the future.

show abstract

“…Strategy 1 was also used for the formation of bicycle 70 through a formal [3 + 4] cycloaddition between enal 64 and azomethine 69 in the presence of NHC 67 and the oxidant 68 (Scheme ) 47. The mechanism is believed to proceed similarly to the one illustrated in Scheme : the vinylogous enolate LVIII , upon nucleophilic addition to imine 69 , forms the [3 + 4] adduct 70 after spontaneous intramolecular lactamization in good yields (51–81%) and enantioselectivities (84–99% ee ).…”

Section: N‐heterocyclic Carbene‐mediated Vinylogous Cascade Processesmentioning

confidence: 99%

Enantioselective Vinylogous Organocascade Reactions

Hepburn

Dell’Amico

Melchiorre

2016

The Chemical Record

100

View full text Add to dashboard Cite

Cascade reactions are powerful tools for rapidly assembling complex molecular architectures from readily available starting materials in a single synthetic operation. Their marriage with asymmetric organocatalysis has led to the development of novel techniques, which are now recognized as reliable strategies for the one-pot enantioselective synthesis of stereochemically dense molecules. In recent years, even more complex synthetic challenges have been addressed by applying the principle of vinylogy to the realm of organocascade catalysis. The key to success of vinylogous organocascade reactions is the unique ability of the chiral organocatalyst to transfer reactivity to a distal position without losing control on the stereo-determining events. This approach has greatly expanded the synthetic horizons of the field by providing the possibility of forging multiple stereocenters in remote positions from the catalyst's point of action with high selectivity while simultaneously constructing multiple new bonds. This article critically describes the developments achieved in the field of enantioselective vinylogous organocascade reactions, charting the ideas, the conceptual advances, and the milestone reactions that have been essential for reaching highly practical levels of synthetic efficiency.

show abstract

N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines

Cited by 235 publications

References 50 publications

N‐Heterocyclic Carbene (NHC)‐Organocatalyzed Kinetic Resolutions, Dynamic Kinetic Resolutions, and Desymmetrizations

N‐Heterocyclic Carbene (NHC)‐Organocatalyzed Kinetic Resolutions, Dynamic Kinetic Resolutions, and Desymmetrizations

Recent Progress in (Dynamic) Kinetic Resolution Catalyzed by N‐Heterocyclic Carbenes

Enantioselective Vinylogous Organocascade Reactions

Contact Info

Product

Resources

About