Enantioselective Rhodium-Catalyzed Isomerization of 4-Iminocrotonates: Asymmetric Synthesis of a Unique Chiral Synthon

Zhang, Wenzhen; Chu, Jifeng; Oberg, Kevin M.; Rovis, Tomislav

doi:10.1021/ja510348p

Cited by 23 publications

(6 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The dihydroxylation and protection of diol was carried out by following a similar protocol available in the literature for 5-isopropoxy-1-(4-methoxybenzyl)-1 H -pyrrol-2(5 H )-one …”

Section: Experimental Sectionmentioning

confidence: 99%

Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes

et al. 2016

View full text Add to dashboard Cite

An unprecedented enantioselective intramolecular oxa-Michael reaction of enols has been described. A squaramide-containing tertiary amine based bifunctional organocatalyst efficiently activates the o-homoformyl chalcones to provide the chiral isochromenes in moderate yields and good to excellent enantioselectivities. Further, late-stage functionalizations of the vinyl ether moiety of the chiral isochromene products have also been exemplified.

show abstract

“…The dihydroxylation and protection of diol was carried out by following a similar protocol available in the literature for 5-isopropoxy-1-(4-methoxybenzyl)-1 H -pyrrol-2(5 H )-one …”

Section: Experimental Sectionmentioning

confidence: 99%

Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes

et al. 2016

View full text Add to dashboard Cite

show abstract

“…N,O-aminals are an interesting class of substituted molecules bearing a geminally N,Osubstituted (stereogenic) carbon center and have been recently recognized as an important class of building blocks in organic synthesis [10]. In the conventional approach, N,O-aminals are derived either from the corresponding α-amido sulfones via nucleophilic substitution, replacing the sulfonyl group with an alkoxy moiety [11][12][13][14][15], or from the corresponding imines by means of nucleophilic addition, introducing an alkoxy group [16][17][18][19][20][21][22][23][24].…”

Section: Bimetallic Approaches To No-aminals and Related Spiro-no-het...mentioning

confidence: 99%

“…The substrate scope was expanded to alkynyl alcohols and alkynyl amines, yielding the desired fused bicyclic N,O-acetals with excellent yield and enantioselectivity. Based on control experiments, a reaction mechanism is proposed: initially, the gold catalyst coordinates with the alkynyl substrate (15) to form a π-gold-alkyne complex (17) and generated the key cyclic intermediate (18) in situ. On the other hand, chiral Lewis acid Ni(II)/L-PiPr 2 -activated β,γ-unsaturated α-ketoester (16) reacts with 18, affording fused bicyclic acetal 19.…”

Section: Bimetallic Approaches To No-aminals and Related Spiro-no-het...mentioning

confidence: 99%

Bimetallic (or Multimetallic) Synthesis of N-Heterocycles

Reis,

Viduedo,

Raydan

et al. 2023

Catalysts

View full text Add to dashboard Cite

Bimetallic (or multimetallic) catalysis has emerged as a powerful tool in modern chemical synthesis, offering improved reaction control and versatility. This review focuses on the recent developments in bimetallic sequential catalysis for the synthesis of nitrogen heterocycles, which are essential building blocks in pharmaceuticals and fine chemicals. The cooperative action of two (sometimes more) different metal catalysts enables intricate control over reaction pathways, enhancing the selectivity and efficiency of the synthesis of N-heterocyclic compounds. By activating less reactive substrates, this multimetal catalytic strategy opens new synthetic possibilities for challenging compounds. The use of catalytic materials in bimetallic systems reduces waste and improves atom efficiency, aligning with green chemistry principles. With a diverse range of metal combinations and reaction conditions, bimetallic catalysis provides access to a broad array of N-heterocyclic compounds with various functionalities. This paper highlights the significant progress made in the past decade in this topic, emphasizing the promising potential of bimetallic catalysis in drug discovery and the fine chemical industries.

show abstract

“…A bulky chiral monophosphoramidite ligand TIPS-Guiphos L84 was developed and applied to the enantioselective cyclization, providing a convenient access to 5-alkyoxy-3-pyrrolin-2-ones ( 240 ) in good yields and excellent enantioselectivities. A possible catalytic cycle was proposed (Scheme ).…”

Section: Asymmetric Coupling Of π-Systemsmentioning

confidence: 99%

Chiral Monophosphorus Ligands for Asymmetric Catalytic Reactions

Tang

2016

ACS Catal.

213

View full text Add to dashboard Cite

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

show abstract

Enantioselective Rhodium-Catalyzed Isomerization of 4-Iminocrotonates: Asymmetric Synthesis of a Unique Chiral Synthon

Cited by 23 publications

References 47 publications

Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes

Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes

Bimetallic (or Multimetallic) Synthesis of N-Heterocycles

Chiral Monophosphorus Ligands for Asymmetric Catalytic Reactions

Contact Info

Product

Resources

About