Diastereoselective 1,4-Conjugate Addition of Alkyl Cuprates to Methyl Cyclopent-1-enecarboxylates

Karlsson, Staffan; Cornwall, Philip; Cruz, Angele; Pontén, Fritiof; Fridén-Saxin, Maria; Turner, Angela

doi:10.1021/acs.oprd.7b00374

Cited by 6 publications

(2 citation statements)

References 23 publications

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“…Taking into account the importance of carbocyclic nucleoside analogs and the bioactivity of peptidyl nucleoside antibiotics containing β-amino acids, our aim was the synthesis of new carbocyclic nucleoside analogs with an amino acid moiety on a β- and γ-lactam basis. This pathway is similar to the first synthesis of carbovir from unsaturated γ-lactam (±)-14 (also known as Vince lactam) [25,26,27]. The synthesis of some 6-membered carbocyclic nucleoside analogs containing γ-amino alcohol was also planned.…”

Section: Resultsmentioning

confidence: 97%

Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs

Remete

Kiss

2019

Molecules

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Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino alcohols with 5-amino-4,6-dichloropyrimidine; ring closure of the formed adduct with HC(OMe)3 and nucleophilic displacement of chlorine with various N-nucleophiles in the resulting 6-chloropurine moiety.

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Section: Resultsmentioning

confidence: 97%

Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs

Remete

Kiss

2019

Molecules

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“…24 Thus, starting from the commercially available VL H , the methylation reaction and the Boc-protected reaction produce the comonomers of VL Me and VL Boc , respectively, in high yields of 96 and 95% (Figure 2). 35,36 Clean 1 H and 13 C NMR spectra (Figure 3) of VL Boc guarantee the efficient olefin copolymerization.…”

Section: ■ Experimental Methodsmentioning

confidence: 92%

Amide-Functionalized Polyolefins and Facile Post-Transformations

Cui

Zhang

et al. 2023

Macromolecules

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Direct copolymerization of olefins with polar monomers to produce functionalized polyolefins has attracted much attention; however, highly efficient incorporation of amide functions into polyolefins is a long-standing challenge because the amide function is pronounced to retard chain growth. In this contribution, Vince Lactam’s derivatives (VL H , VL Me , and VL Boc ) that contain high ring strain and an amide moiety are utilized in ethylene copolymerization mediated by palladium catalysts. Amide-functionalized polyethylenes, poly(E-VLBoc)s, are accessible with key characteristics of high amide incorporations (up to 30.1 mol %), high copolymer molecular weights, and high catalytic activities. The incorporation of the amide comonomer converts crystalline poly(E-VLBoc)s (T m = 115–125 °C) to noncrystalline and transparent poly(E-VLBoc)s (T g = 98–196 °C, optical transmittance (T) = 87.6%–90.4%). Both characteristics of cyclic amide functions and high amide incorporations in poly(E-VLBoc) enable facile post-transformations under mild conditions to produce hydrogen bond-containing (-C(O)NH-) poly(E-VLH), difunctionalized (-COOH and -NHR) poly(E-VLNHBoc), and water-soluble ammonium-functionalized poly(E-VLNH3 + ). The ammonium functionality endows polyolefin with antibacterial properties.

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Stereocontrolled Synthesis of Fluorine‐Containing Piperidine γ‐Amino Acid Derivatives

et al. 2018

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An efficient synthetic approach for the construction of fluorine‐containing piperidine γ‐amino acid derivatives has been developed. The synthetic concept was based on oxidative ring opening of an unsaturated bicyclic γ‐lactam (Vince‐lactam) through its ring C=C bond, followed by double reductive amination of the diformyl intermediate performed with various fluoroalkylamines. The method has been extended towards the access of alkylated and perfluoroalkylated substances and for γ‐lactam derivatives. The transformations proceeded with stereocontrol: the configuration of the stereocenters in the products were predetermined by the configuration of the chiral centers of the starting γ‐lactam. The method could be extended for the access to enantiopure piperidine γ‐amino esters.

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Diastereoselective 1,4-Conjugate Addition of Alkyl Cuprates to Methyl Cyclopent-1-enecarboxylates

Cited by 6 publications

References 23 publications

Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs

Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs

Amide-Functionalized Polyolefins and Facile Post-Transformations

Stereocontrolled Synthesis of Fluorine‐Containing Piperidine γ‐Amino Acid Derivatives

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