Cargando…

Synthesis of β(2,2)-Amino Acids by Stereoselective Alkylation of Isoserine Derivatives Followed by Nucleophilic Ring Opening of Quaternary Sulfamidates

[Image: see text] Chiral bicyclic N,O-acetal isoserine derivatives have been synthesized by an acid-catalyzed tandem N,O-acetalization/intramolecular transcarbamoylation reaction between conveniently protected l-isoserine and 2,2,3,3-tetramethoxybutane. The delicate balance of the steric interaction...

Descripción completa

Detalles Bibliográficos
Autores principales:	Tovillas, Pablo, Navo, Claudio D., Oroz, Paula, Avenoza, Alberto, Corzana, Francisco, Zurbano, María M., Jiménez-Osés, Gonzalo, Busto, Jesús H., Peregrina, Jesús M.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2022
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490828/ https://www.ncbi.nlm.nih.gov/pubmed/35732024 http://dx.doi.org/10.1021/acs.joc.2c01034

Ejemplares similares

Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine
por: Oroz, Paula, et al.
Publicado: (2022)

Synthesis of Fluorescent Lanthipeptide Cytolysin S Analogues by Late-Stage Sulfamidate Ring Opening
por: Mazo, Nuria, et al.
Publicado: (2023)

Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters
por: Chen, Xu, et al.
Publicado: (2022)

The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines
por: Pham, Quoc Hoang, et al.
Publicado: (2021)

Benzylsulfamide
por: Gelbrich, Thomas, et al.
Publicado: (2011)

Highly stereoselective nickel-catalyzed difluoroalkylation of aryl ketones to tetrasubstituted monofluoroalkenes and quaternary alkyl difluorides
por: Li, Chao, et al.
Publicado: (2019)

Quaternary stereocentres via catalytic enantioconvergent nucleophilic substitution reactions of tertiary alkyl halides by alkenylmetal reagents
por: Wang, Zhaobin, et al.
Publicado: (2021)

Synthesis of New Fused Benzothiadiazepines and Macrocyclic Sulfamides Starting from N,N-Disubstituted Sulfamides and N(Boc)-Sulfamides
por: Dehamchia, Mohamed, et al.
Publicado: (2012)

Synthesis, conformational analysis and in vivo assays of an anti-cancer vaccine that features an unnatural antigen based on an sp(2)-iminosugar fragment
por: Bermejo, Iris A., et al.
Publicado: (2020)

Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres
por: Lanke, Veeranjaneyulu, et al.
Publicado: (2020)

Heterolysis of Dihydrogen by Nucleophilic Calcium Alkyls
por: Wilson, Andrew S. S., et al.
Publicado: (2018)

Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation
por: Ferhati, Xhenti, et al.
Publicado: (2021)

Mucin architecture behind the immune response: design, evaluation and conformational analysis of an antitumor vaccine derived from an unnatural MUC1 fragment
por: Martínez-Sáez, Nuria, et al.
Publicado: (2016)

Few layer 2D pnictogens catalyze the alkylation of soft nucleophiles with esters
por: Lloret, Vicent, et al.
Publicado: (2019)

Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Sulfamidate Imines: Efficient Synthesis of Chiral Cyclic Sulfamidates
por: Liu, Yuanhua, et al.
Publicado: (2019)

Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids
por: Yang, Tianyi, et al.
Publicado: (2018)

Palladium-catalyzed asymmetric allylic alkylation (AAA) with alkyl sulfones as nucleophiles
por: Trost, Barry M., et al.
Publicado: (2021)

Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Aminoalkyl)boronic Esters
por: Ursinyova, Nina, et al.
Publicado: (2015)

Nucleophilic trifluoromethoxylation of alkyl halides without silver
por: Li, Yan, et al.
Publicado: (2020)

Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution
por: Antoniak, Damian, et al.
Publicado: (2022)

Iridium-catalysed direct sulfamidation of quinazolinones
por: Feng, Yadong, et al.
Publicado: (2018)

General Allylic C–H Alkylation with Tertiary Nucleophiles
por: Howell, Jennifer M., et al.
Publicado: (2014)

Substrate Control in Stereoselective Lanthionine Biosynthesis
por: Tang, Weixin, et al.
Publicado: (2014)

Deciphering the Non-Equivalence of Serine and Threonine O-Glycosylation Points: Implications for Molecular Recognition of the Tn Antigen by an anti-MUC1 Antibody**
por: Martínez-Sáez, Nuria, et al.
Publicado: (2015)

Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers
por: Chen, Xu, et al.
Publicado: (2022)

NHC and nucleophile chelation effects on reactive iron(ii) species in alkyl–alkyl cross-coupling
por: Fleischauer, Valerie E., et al.
Publicado: (2018)

Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement
por: Crimmins, Michael T., et al.
Publicado: (2014)

Enantioselective N-heterocyclic carbene-catalyzed nucleophilic dearomatization of alkyl pyridiniums
por: Flanigan, Darrin M., et al.
Publicado: (2017)

Microbial alkyl- and aryl-sulfatases: mechanism, occurrence, screening and stereoselectivities
por: Toesch, Michael, et al.
Publicado: (2013)

Regio- and Stereoselective Electrochemical Alkylation of Morita–Baylis–Hillman Adducts
por: Bertuzzi, Giulio, et al.
Publicado: (2022)

Visible light-driven Giese reaction with alkyl tosylates catalysed by nucleophilic cobalt
por: Komeyama, Kimihiro, et al.
Publicado: (2021)

Mechanism of the Stereoselective α-Alkylation of Aldehydes Driven by the Photochemical Activity of Enamines
por: Bahamonde, Ana, et al.
Publicado: (2016)

Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters
por: Pérez-Palau, Marina, et al.
Publicado: (2021)

Nickel-Catalyzed Stereoselective Coupling Reactions of Benzylic and Alkyl Alcohol Derivatives
por: Herbert, Claire A., et al.
Publicado: (2023)

Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations
por: Mitsudo, Koichi, et al.
Publicado: (2018)

4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions
por: Burns, Michael J, et al.
Publicado: (2014)

Novel Sulfamide-Containing Compounds as Selective Carbonic Anhydrase I Inhibitors
por: Berrino, Emanuela, et al.
Publicado: (2017)

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces
por: Pantaine, Loïc, et al.
Publicado: (2017)

Toxicity evaluation of sulfamides and coumarins that efficiently inhibit human carbonic anhydrases
por: Aspatwar, Ashok, et al.
Publicado: (2020)

Sulfamides direct radical-mediated chlorination of aliphatic C–H bonds
por: Short, Melanie A., et al.
Publicado: (2019)

Cannot write session to /tmp/vufind_sessions/sess_qcca0ft0lbh5rj8ebpom0g6psh