Rearrangement of oxazolidinethiones to thiazolidinediones or thiazinanediones and their application for the synthesis of chiral allylic ureas and α-methyl-β-amino acids

Sabala, Rocio; Hernández, J. Sánchez; Carranza, Vladimir; Meza-León, Rosa L.; Bernès, Syl­vain; Sansinenea, Estibaliz; Ortíz, Aurelio

doi:10.1016/j.tet.2009.11.035

Cited by 8 publications

(8 citation statements)

References 49 publications

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“…Amino acids 5 were formed from 4 by Ru catalyzed oxidation . To facilitate isolation and characterization, the corresponding esters 6 were formed by carboxylate methylation.…”

Section: Resultsmentioning

confidence: 99%

“…27 Amino acids 5 were formed from 4 by Ru catalyzed oxidation. 28 To facilitate isolation and characterization, the corresponding esters 6 were formed by carboxylate methylation. All products 6 were isolated in diastereomerically pure form by crystallization from n-hexane.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In analogy to a literature procedure, , the corresponding Cbz-protected β-amino acid 5 (1.0 equiv) and DMF (2–3 drops) were dissolved in DCM (20 mL/mmol substrate). Oxalyl chloride (1.25 equiv) was added dropwise and the solution was stirred at 22 °C for 2 h. After the solvent was removed under reduced pressure the crude oil was dissolved in benzene (20 mL/mmol substrate).…”

Section: Experimental Sectionmentioning

confidence: 99%

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Enantioenriched γ-Aminoalcohols, β-Amino Acids, β-Lactams, and Azetidines Featuring Tetrasubstituted Fluorinated Stereocenters via Palladacycle-Catalyzed Asymmetric Fluorination of Isoxazolinones

et al. 2021

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Enantiopure fluorine containing β-amino acids are of large biological and pharmaceutical interest. Strategies to prepare β-amino acid derivatives possessing a F-containing tetrasubstituted stereocenter at the α-C atom in a catalytic asymmetric sense are rare, in particular using an enantioselective electrophilic C–F bond formation. In the present study, a highly enantioselective palladacycle-catalyzed fluorination of isoxazolinones was developed. It is demonstrated that isoxazolinones are useful precursors toward enantiopure β-amino acid derivatives by diastereo- and chemoselective reduction. The formed γ-aminoalcohols served as valuable precursors toward β-amino acids, β-amino acid esters, and β-lactams, all featuring tetrasubstituted fluorinated stereocenters. In addition, by this work, enantioenriched fluorinated azetidines were accessible for the first time.

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“…Amino acids 5 were formed from 4 by Ru catalyzed oxidation . To facilitate isolation and characterization, the corresponding esters 6 were formed by carboxylate methylation.…”

Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

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Enantioenriched γ-Aminoalcohols, β-Amino Acids, β-Lactams, and Azetidines Featuring Tetrasubstituted Fluorinated Stereocenters via Palladacycle-Catalyzed Asymmetric Fluorination of Isoxazolinones

et al. 2021

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confidence: 99%

“…Therefore, a selection of amino alcohols products (3) from the aza-Wacker reaction were oxidized to the β-amino acids 5 in near quantitative yields, with no significant erosion of the enantiomeric ratio (Table 3). 18 In summary, we have developed a Markovnikov addition of carbamates to tri-and disubstituted olefins. This Pd-catalyzed reaction generates α-tertiary and α-secondary β-amino alcohols in moderate yields and moderate to good enantioselectivities, from which facile oxidation permits access to β-amino acids.…”

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confidence: 99%

Enantioselective Markovnikov Addition of Carbamates to Allylic Alcohols for the Construction of α-Secondary and α-Tertiary Amines

et al. 2019

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Herein we describe the development of a Pd-catalyzed enantioselective Markovnikov addition of carbamates to allylic alcohols for the construction of α-tertiary and α-secondary amines. The reaction affords a range of β-amino alcohols, after reduction of the aldehyde in situ, which contain a variety of functional groups in moderate yields and moderate to good enantioselectivities. These products can be readily oxidized to β-amino acids, valuable building blocks for the synthesis of biologically active compounds. Mechanistic studies indicate that C–N bond formation occurs via a syn amino-palladation mechanism, an insight which may guide future reaction development given the limited number of enantioselective syntheses of α-tertiary amines.

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3.2 Amino Acid Derived Heterocyclic Chiral Auxiliaries: The use of Oxazolidinones, Oxazolidinethiones, Thiazolidinethiones, and Imidazolidinones

Shamszad

Crimmins

2012

Comprehensive Chirality

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Rearrangement of oxazolidinethiones to thiazolidinediones or thiazinanediones and their application for the synthesis of chiral allylic ureas and α-methyl-β-amino acids

Cited by 8 publications

References 49 publications

Enantioenriched γ-Aminoalcohols, β-Amino Acids, β-Lactams, and Azetidines Featuring Tetrasubstituted Fluorinated Stereocenters via Palladacycle-Catalyzed Asymmetric Fluorination of Isoxazolinones

Enantioenriched γ-Aminoalcohols, β-Amino Acids, β-Lactams, and Azetidines Featuring Tetrasubstituted Fluorinated Stereocenters via Palladacycle-Catalyzed Asymmetric Fluorination of Isoxazolinones

Enantioselective Markovnikov Addition of Carbamates to Allylic Alcohols for the Construction of α-Secondary and α-Tertiary Amines

3.2 Amino Acid Derived Heterocyclic Chiral Auxiliaries: The use of Oxazolidinones, Oxazolidinethiones, Thiazolidinethiones, and Imidazolidinones

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