Catalytic Asymmetric Total Synthesis of (−)‐Galanthamine and (−)‐Lycoramine

Li, Lei; Qiao, Yingjie; Wang, Yuan; Jia, Yanxing

doi:10.1002/ange.201411338

Cited by 22 publications

(1 citation statement)

References 60 publications

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“…Remarkably, Feng N , N '‐dioxide L 3 ‐PrPr 2 was successfully applied in total synthesis by the Jia group in 2015. [ 60 ] The optically pure 3,3‐disubstituted benzofuranones possessing a chiral quaternary carbon center were obtained through L 3 ‐PrPr 2 ‐Sc(III) catalyzed Michael addition of benzofuranones to methyl vinyl ketones in excellent yields and enantioselectivity (Scheme 23). This developed protocol was further utilized in the catalytic asymmetric total synthesis of (–)‐galanthamine and (–)‐lycoramine.…”

Section: Studies By Other Groupsmentioning

confidence: 99%

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Wang

2021

Chin. J. Chem.

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Feng ligand | N,N'-Dioxide | O ligands | Asymmetric catalysis | Lewis acids Catalysts and ligands possessing the great ability to tolerate over a wide range of mechanistically unrelated reactions are remarked as "privileged", which are rather scarce but extremely meaningful in asymmetric catalysis. Feng and co-workers have developed a library of conformationally flexible, C 2-symmetric N,N'-dioxide amide compounds with original design and featured structure (named as Feng ligand now). They were initially reported as chiral organocatalysts in 2005 and have been further developed as a new class of privileged chiral ligands since 2006. Tremendous success, including versatile coordination chemistry with plenty of metal sources (main-group metals, transition metals, and rare-earth metals), a truly broad scope of asymmetric reactions (more than 50 types), diverse areas of catalysis (organocatalysis, Lewis-acid catalysis, bimetallic relay catalysis, and photocatalysis), numerous synthetic applications of bioactive compounds, has been achieved using Feng N,N'-dioxide. Besides, they demonstrate that chiral ligands with conformationally flexible property can offer excellent chiral environment as well, which challenges the conventional idea preferring rigid structures in the design of chiral ligands. Herein, we briefly introduced the discovery of Feng ligand and the millstones during the development. We also covered the successful applications of Feng ligand by other scientists as well as novel chiral ligands inspired by them. Contents 1. Introduction 969 2. Initial Discovery 970 3. Representative Applications 971 3.1. Classical asymmetric reactions 971 3.2. Novel asymmetric reactions 975 4. Studies by Other Groups 977 4.1. Reactions using Feng ligand 977 4.2. Novel chiral ligands inspired by Feng ligand 980 5. Conclusions 980

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Section: Studies By Other Groupsmentioning

confidence: 99%

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Wang

2021

Chin. J. Chem.

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Asymmetric Conjugate Addition of Benzofuran‐2‐ones to Alkyl 2‐Phthalimidoacrylates: Modeling Structure–Stereoselectivity Relationships with Steric and Electronic Parameters

Yang

Zhang

et al. 2016

Angewandte Chemie

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Ahighly predictive model to correlate the steric and electronic parameters of tertiary amine thiourea catalysts with the stereoselectivity of Michael reactions of 3-substituted benzofuranones and alkyl 2-phthalimidoacrylates is described. As predicted, new 3,5-bis(trifluoromethyl)benzyl-and methylsubstituted tertiary amine thioureas turned out to be highly suitable catalysts for this reaction and enabled the synthesis of enantioenriched a-amino acid derivatives with 1,3-nonadjacent stereogenic centers.

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trans‐Carbocarbonation of Internal Alkynes through a Formal anti‐Carbopalladation/C−H Activation Cascade

2018

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An intramolecular Pd‐catalyzed cascade reaction is presented that consists of a formal anti‐carbopalladation of a C−C triple bond followed by C−H activation. As a result, oligocyclic ring systems with an embedded tetrasubstituted double bond are formed. The key to success in affording the trans geometry of the emerging double bond are alkyne units with residues that must not undergo β‐hydride elimination (e.g., t‐butyl or silyl groups). Silyl groups proved to be a perfect handle to further convert the tetrasubstituted alkenes. The evaluation of kinetic data with a deuterium‐labeled compound and X‐ray analyses of trapped intermediates provided additional insight into the catalytic cycle.

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Catalytic Asymmetric Total Synthesis of (−)‐Galanthamine and (−)‐Lycoramine

Cited by 22 publications

References 60 publications

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Asymmetric Conjugate Addition of Benzofuran‐2‐ones to Alkyl 2‐Phthalimidoacrylates: Modeling Structure–Stereoselectivity Relationships with Steric and Electronic Parameters

trans‐Carbocarbonation of Internal Alkynes through a Formal anti‐Carbopalladation/C−H Activation Cascade

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