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Showing 1 to 12 of 28 entries
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Stereochemical aspects and the synthetic scope of the S(H)i at the sulfur atom. Preparation of enantiopure 3-substituted 2,3-dihydro-1,2-benzoisothiazole 1-oxides and 1,1-dioxides.

Chemical communications (Cambridge, England)

Fernández-Salas JA, Rodríguez-Fernández MM, Maestro MC, García-Ruano JL.
PMID: 24769863
Chem Commun (Camb). 2014 Jun 07;50(45):6046-8. doi: 10.1039/c4cc01831a. Epub 2014 Apr 28.

Intramolecular homolytic substitution (SHi) on the sulfur atom at acyclic N-(o-bromobenzyl)sulfinamides takes place with a complete inversion of the configuration and provides an excellent tool to connect N-tert-butanesulfinylimines with enantiopure 3-substituted benzo-fused sulfinamides (1,2-benzoisothiazoline 1-oxides) and the related pharmacologically...

Remote stereocontrol mediated by a sulfinyl group: synthesis of allylic alcohols via chemoselective and diastereoselective reduction of gamma-methylene delta-ketosulfoxides.

The Journal of organic chemistry

García Ruano JL, Fernández-Ibáñez MA, Fernández-Salas JA, Maestro MC, Márquez-López P, Rodríguez-Fernández MM.
PMID: 19113884
J Org Chem. 2009 Feb 06;74(3):1200-4. doi: 10.1021/jo802378s.

The efficiency of the sulfinyl group as a remote controller of the chemoselectivity and diastereoselectivity of the reduction of alpha, beta-unsaturated alpha-[2-(p-tolylsulfinyl)phenyl] substituted ketones 1 has been demonstrated in reactions carried out under NaBH4 in the presence of Yb(OTf)3...

Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes.

ACS catalysis

Esteban F, Cieślik W, Arpa EM, Guerrero-Corella A, Díaz-Tendero S, Perles J, Fernández-Salas JA, Fraile A, Alemán J.
PMID: 29527400
ACS Catal. 2018 Mar 02;8(3):1884-1890. doi: 10.1021/acscatal.7b03553. Epub 2018 Jan 31.

An organocatalytic strategy for the synthesis of tetrasubstituted pyrrolidines with monoactivated azomethine ylides in high enantiomeric excess and excellent exo/endo selectivity is presented. The key to success is the intramolecular activation via hydrogen bonding through an

Asymmetric [2,3]-Wittig Rearrangement: Synthesis of Homoallylic, Allenylic, and Enynyl α-Benzyl Alcohols.

Organic letters

Rodríguez RI, Ramírez E, Fernández-Salas JA, Sánchez-Obregón R, Yuste F, Alemán J.
PMID: 30525700
Org Lett. 2018 Dec 21;20(24):8047-8051. doi: 10.1021/acs.orglett.8b03659. Epub 2018 Dec 10.

A highly stereoselective [2,3]-Wittig rearrangement of allylic and propargylic ethers controlled by a chiral sulfoxide moiety is presented. The activation provided by the sulfoxide at the remote ortho position allows the rearrangement of less-activated and unexplored benzylic carbanions. Thus,...

Nucleophilic halo-Michael addition under Lewis-base activation.

Chemical communications (Cambridge, England)

Laina-Martín V, Pérez I, Fernández-Salas JA, Alemán J.
PMID: 31599898
Chem Commun (Camb). 2019 Oct 24;55(86):12936-12939. doi: 10.1039/c9cc07068k.

A simple and general conjugate nucleophilic halogenation is presented. The THTO/halosilane combination has shown the ability to act as a nucleophilic halide source in the conjugate addition to a variety of Michael acceptors. In addition, a straightforward diastereoselective halogen...

Metal-free C-H thioarylation of arenes using sulfoxides: a direct, general diaryl sulfide synthesis.

Chemical communications (Cambridge, England)

Fernández-Salas JA, Pulis AP, Procter DJ.
PMID: 27722278
Chem Commun (Camb). 2016 Oct 11;52(83):12364-12367. doi: 10.1039/c6cc07627k.

Metal-free C-H thioarylation of arenes and heteroarenes using methyl sulfoxides constitutes a general protocol for the synthesis of high value diaryl sulfides. The coupling of arenes and heteroarenes with in situ activated sulfoxides is regioselective, uses readily available starting...

Iridium(I) hydroxides in catalysis: rearrangement of allylic alcohols to ketones.

Organic & biomolecular chemistry

Nelson DJ, Fernández-Salas JA, Truscott BJ, Nolan SP.
PMID: 25031155
Org Biomol Chem. 2014 Sep 14;12(34):6672-6. doi: 10.1039/c4ob01428f.

The iridium(I) hydroxide complex [Ir(OH)(COD)(I(i)Pr)] has been shown to be a competent catalyst for the rearrangement of allylic alcohols to ketones. Reactions proceed in short reaction times (1-1.5 h) with microwave heating, in the absence of additives.

Asymmetric synthesis of Rauhut-Currier-type esters via Mukaiyama-Michael reaction to acylphosphonates under bifunctional catalysis.

Chemical communications (Cambridge, England)

Laina-Martín V, Del Río-Rodríguez R, Díaz-Tendero S, Fernández-Salas JA, Alemán J.
PMID: 30387790
Chem Commun (Camb). 2018 Dec 11;54(99):13941-13944. doi: 10.1039/c8cc07561a.

A highly enantioselective organocatalytic Mukaiyama-Michael reaction of silyloxy dienes and α,β-unsaturated acyl phosphonates under bifunctional organocatalysis is presented. The new reactivity triggered by the catalyst conducted to Rauhut-Currier type esters, via a formal conjugate addition to α,β-unsaturated esters. This...

Molecular Characterization of Associated Pathogens in Febrile Patients during Inter-Epidemic Periods of Urban Arboviral Diseases in Tapachula Southern Mexico.

Pathogens (Basel, Switzerland)

Calvo-Anguiano G, Lugo-Trampe JJ, Ponce-García G, Lugo-Trampe A, Martinez-Garza LE, Ibarra-Ramirez M, Campos-Acevedo LD, Caballero-Sosa S, Juache-Villagrana AE, Fernández-Salas I, Flores-Suarez AE, Rodriguez-Sanchez IP, Trujillo-Murillo KDC.
PMID: 34832606
Pathogens. 2021 Nov 08;10(11). doi: 10.3390/pathogens10111450.

Emerging and re-emerging vector-borne infections are a global public health threat. In endemic regions, fever is the main reason for medical attention, and the etiological agent of such fever is not usually identified. In this study, non-specific febrile pathogens...

Enantioselective vinylogous-Mukaiyama-type dearomatisation by anion-binding catalysis.

Chemical communications (Cambridge, England)

Kaur K, Humbrías-Martín J, Hoppmann L, Fernández-Salas JA, Daniliuc CG, Alemán J, Mancheño OG.
PMID: 34519302
Chem Commun (Camb). 2021 Sep 14;57(73):9244-9247. doi: 10.1039/d1cc03514b.

The first enantioselective vinylogous Mukaiyama-type dearomatisation of heteroarenes under anion-binding catalysis is presented. A recyclable tetrakistriazole catalyst was used for the enantiocontrol of the remote vinylogous active position of silyl dienol ethers. This approach provided chiral heterocycles bearing α,β-unsaturated...

A cationic ruthenium complex for the dynamic kinetic resolution of secondary alcohols.

Chemistry (Weinheim an der Bergstrasse, Germany)

Fernández-Salas JA, Manzini S, Nolan SP.
PMID: 25167839
Chemistry. 2014 Oct 06;20(41):13132-5. doi: 10.1002/chem.201404096. Epub 2014 Aug 28.

A synthetic protocol making use of a well-defined cationic ruthenium complex 2 enabling the racemization of enantiomerically pure secondary alcohols in the presence of a weak base (K2CO3) is described. The compatibility of 2 with Candida Antarctica lipase B...

Metal-Free CH-CH-Type Cross-Coupling of Arenes and Alkynes Directed by a Multifunctional Sulfoxide Group.

Journal of the American Chemical Society

Fernández-Salas JA, Eberhart AJ, Procter DJ.
PMID: 26745643
J Am Chem Soc. 2016 Jan 27;138(3):790-3. doi: 10.1021/jacs.5b12579. Epub 2016 Jan 14.

A metal-free CH-CH-type coupling of arenes and alkynes, mediated by a multifunctional sulfoxide directing group, exploits nonprefunctionalized coupling partners, proceeds under mild conditions, is operationally simple, and exhibits high functional group tolerance. The products of the CH-CH coupling are...

Showing 1 to 12 of 28 entries