Tertiary Amine Lewis Base Catalysis in Combination with Transition Metal Catalysis

Knox, Gary J.; Hutchings-Goetz, Luke S; Pearson, Colin M.; Snaddon, Thomas N.

doi:10.1007/s41061-020-0279-7

Cited by 28 publications

(5 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, Snaddon has reviewed the general combination of chiral tertiary amine Lewis base catalysis with chiral transition metal catalysis. 14 This review will inspect developments since 2016 in the deployment of a chiral aminocatalyst with an achiral metal catalyst. Specifically, the reactions we will analyse here are examples of 'Type I' systems in which each catalyst acts independently and fully cooperatively.…”

Section: Christian D-t Nielsenmentioning

confidence: 99%

Recent progress in asymmetric synergistic catalysis – the judicious combination of selected chiral aminocatalysts with achiral metal catalysts

et al. 2022

View full text Add to dashboard Cite

show abstract

Section: Christian D-t Nielsenmentioning

confidence: 99%

Recent progress in asymmetric synergistic catalysis – the judicious combination of selected chiral aminocatalysts with achiral metal catalysts

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Despite the steep trajectory of advances in this arena, strategically leveraging π‐bond activation by M−H species in conjunction with Lewis base catalysis within the framework of enantioselective cooperative catalysis remains conspicuously underdeveloped [2] . Our interest in combining transition metal‐ and Lewis base organocatalysis [3–5] presented an opportunity to reconcile this disparity and in so doing unveil new avenues to expedite the synthesis of motifs that are common to an array of bioactive molecules such as polyketides. Established aldol preparations typically proceed via the same general template in which enolates (or enolate equivalents) react with aldehyde electrophiles (Figure 1a) [6] .…”

Section: Figurementioning

confidence: 99%

A Pd−H/Isothiourea Cooperative Catalysis Approach to anti‐Aldol Motifs: Enantioselective α‐Alkylation of Esters with Oxyallenes**

et al. 2022

Self Cite

View full text Add to dashboard Cite

The biological and therapeutic significance of natural products is a powerful impetus for the development of efficient methods to facilitate their construction. Accordingly, and reflecting the prevalence of β‐oxy‐carbonyl motifs, a sophisticated arsenal of aldol‐based strategies has evolved that is contingent on the generation of single enolate isomers. Since this has the potential to compromise efficiency in reagent‐based paradigms, direct catalysis‐based solutions would be enabling. To complement the array of substrate‐based strategies, and regulate enolate geometry at the catalyst level, a direct catalytic alkylation of esters with oxyallenes has been developed. Synergizing metal hydride reactivity with Lewis base catalysis has resulted in a broad reaction scope with useful levels of stereocontrol (up to >99 % ee). Facile derivatization of these ambiphilic linchpins is demonstrated, providing access to high‐value vicinal stereocenter‐containing motifs, including 1,2‐amino alcohols.

show abstract

“…Chemists have exploited cooperative and relay catalytic systems involving a transition metal with a Lewis base and demonstrated their great potential in asymmetric catalysis. In these processes, tertiary amines 30 – 33 , phosphines 34 , 35 , N -heterocyclic carbenes (NHCs) 36 – 39 , and isothioureas 40 – 54 were successfully utilized as Lewis base catalysts (Fig. 1A ).…”

Section: Introductionmentioning

confidence: 99%

Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors

Jiang

Zhang

et al. 2023

Commun Chem

View full text Add to dashboard Cite

Significant progress has been made in asymmetric synthesis through the use of transition metal catalysts combined with Lewis bases. However, the use of a dual catalytic system involving 4-aminopyridine and transition metal has received little attention. Here we show a metal/Lewis base relay catalytic system featuring silver acetate and a modified chiral pyrrolidinopyridine (PPY). It was successfully applied in the cycloisomerization/(2 + 3) cycloaddition reaction of enynamides. Bispirocyclopentene pyrazolone products could be efficiently synthesized in a stereoselective and economical manner (up to >19:1 dr, 99.5:0.5 er). Transformations of the product could access stereodivergent diastereoisomers and densely functionalized polycyclic derivatives. Mechanistic studies illustrated the relay catalytic model and the origin of the uncommon chemoselectivity. In subsequent bioassays, the products containing a privileged drug-like scaffold exhibited isoform-selective phosphodiesterase 1 (PDE1) inhibitory activity in vitro. The optimal lead compound displayed a good therapeutic effect for ameliorating pulmonary fibrosis via inhibiting PDE1 in vivo.

show abstract

Tertiary Amine Lewis Base Catalysis in Combination with Transition Metal Catalysis

Cited by 28 publications

References 40 publications

Recent progress in asymmetric synergistic catalysis – the judicious combination of selected chiral aminocatalysts with achiral metal catalysts

Recent progress in asymmetric synergistic catalysis – the judicious combination of selected chiral aminocatalysts with achiral metal catalysts

A Pd−H/Isothiourea Cooperative Catalysis Approach to anti‐Aldol Motifs: Enantioselective α‐Alkylation of Esters with Oxyallenes**

Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors

Contact Info

Product

Resources

About