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Water-Compatible Synthesis of 2-trifluoromethyl-1,3-Dioxanes
Liliana Becerra-Figueroa, Alexander F. Tiniakos, Joëlle Prunet and Diego Gamba-Sánchez
Eur. J. Org. Chem, 2018, 6929-6932.
DOI:10.1002/ejoc.201801367 More...

Communication

A water-compatible method for the diastereoselective synthesis of 2-trifluormethyl-1,3-dioxanes is described. The reaction proceeds under mild reaction conditions using simple inorganic bases; it has a very good substrate scope and can be performed with different Michael acceptors.

Direct Transamidation Reactions: Mechanism and Recent Advances
Paola Acosta-Guzmán, Alejandra Mateus-Gomez and Diego Gamba-Sánchez
Molecules, 23, 2018, 2382.
DOI: 10.3390/molecules23092382 More...

Review / Book Chapter

In this review, we present research on direct transamidation reactions ranging from studies of the mechanism to the recent developments of more applicable and versatile methodologies, emphasizing those reactions involving activation with metal catalysts. Wrote by invitation
Book Chapter in Amide Bond Activation

Synthesis of 1,3-diols by O-nucleophile Additions to Activated Alkenes
Diego Gamba-Sánchez and Joëlle Prunet
Synthesis, 50, 2018, 3997-4007.
DOI: 10.1055/s-0037-1610248 More...

Short Review

This review focuses on homoallylic alcohol substrates that react with a relay compound to form an intermediate oxygen nucleophile, which in turn will lead to a protected 1,3-diol by intramolecular addition to the olefin moiety. Wrote by invitation

Whole Cells as Biocatalyst in Organic Transaformations
Fabian Garzón-Posse, Liliana Becerra-Figueroa, José Hernandez-Arias and Diego Gamba-Sánchez
Molecules, 23, 2018, 1265-1302.
DOI: 10.1039/molecules23061265 More...

Review

This review surveys the most recent developments in the enantioselective reduction of carbon-carbon double bonds and prochiral ketones and the oxidation of sulfides using wholle cells as biocatalytic systems.

Intramolecular Oxa-Michael Reaction on α,β-unsaturated α-amino-δ-hydroxycarboxylic Acid Esters. Synthesis of functionalized 1,3-dioxanes
Liliana Becerra-Figueroa, Santiago Movilla, Joëlle Prunet, Gian Pietro Miscione and Diego Gamba-Sánchez
Org. Biomol. Chem., 16, 2018, 1277-1286.
DOI: 10.1039/C6OB02333A More...

Full Paper

A simple and selective method to access 1,3-dioxanes functionalized in positions 2,4 and 6 has been developed. The experimental results are complemented with a complete DFT study on the reaction mechanism, which illustrates the reaction course and explains the reactivity and selectivity.

Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction
Liliana Becerra-Figueroa, Elodie Brun, Michael Mathieson, Louis Farrugia, Claire Wilson, Joëlle Prunet and Diego Gamba-Sánchez
Org. Biomol. Chem., 7, 2017, 301-3015.
DOI: 10.1039/C6OB02333A More...

Communication

A rapid and simple method to access trifluoromethylated 1,3-dioxanes by a sequence addition/oxa-Michael reaction has been developed; the reaction proceeds smoothly with excellent stereo selectivity.

Recent developments in amide synthesis using non-activated starting materials
Andrea Ojeda-Porras and Diego Gamba-Sánchez
J. Org. Chem. 81, 2016, 11548-11555.
DOI: 10.1021/acs.joc.6b02358 More...

Synopsis

A brief review on recent developments in amide syntesis is presnted. The examples are very recent and were carefully selected based on its wide scope and innovative approach.

Insights into the Pummerer synthesis of oxazolines
Laura Becerra-Cely, Juan Rueda-Espinosa, Andrea Ojeda-Porras and Diego Gamba-Sánchez
Org. Biomol. Chem. 14, 2016, 8474-8485.
DOI: 10.1039/C6OB01666A More...

Full Paper

A rapid and simple method to access unnatural 2-substituted 5-thio oxazolines has been developed using Pummerer chemistry.

Pummerer-type Reactions as Powerful Tools in Organic Synthesis
Diego Gamba-Sánchez and Fabián Garzón-Posse
Molecular Rearrangements in Organic Synthesis, Ed. C. Rojas. Wiley, 2015, CH 20, pp. 661-702
ISBN: 978-1-118-34796-6 More...




Book Chapter

A survey on recent and carefully selected examples describing the use of Pummerer-type reactions is presented. Wrote by invitation
Reviewed by Angewandte Chemie More...
Transamidation of thioacetamide catalyzed by SbCl3
Andrea Ojeda-Porras and Diego Gamba-Sánchez.
Tetrahedron Lett. 56, 2015, 4308-4311.
DOI: 10.1016/j.tetlet.2015.05.067 More...

Communication

Catalytic amounts of SbCl3 notably increases the yields and diminishes the reaction times for transamidation reaction of thioacetamide.

Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support
Andrea Ojeda-Porras, Alejandra Hernandez-Santana and Diego Gamba-Sánchez.
Green Chem. 17, 2015, 3157-3163.
DOI: 10.1039/C5GC00189G More...

Full Paper

A highly improved and green methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. Several examples using aliphatic, aromatic, unsaturated and fatty acids combined with primary and secondary amines are shown.

Transamidation of carboxamides catalyzed by Fe(III) and water
Liliana Becerra-Figueroa, Andrea Ojeda-Porras and Diego Gamba-Sánchez.
J. Org. Chem. 79, 2014, 4544-4552.
DOI: 10.1021/jo500562w More...

Full Paper

The highly efficient transamidation of several primary, secondary, and tertiary amides with aliphatic and aromatic amines (primary and secondary) is described. The reaction is performed in the presence of a 5 mol % concentration of different hydrated salts of Fe(III), and the results show that the presence of water is crucial.

Fumagillin and structurally related molecules as source of new drugs
Diego Gamba-Sánchez,
Mini Rev. Org. Chem. 9, 2012, 126-142.
DOI: 10.2174/157019312800604724 More...

Mini-Review

A survey in the total synthesis of fumagillin and structurally related molecules is presented, also a discussion about the SAR studies is included.

Hydrogen Peroxide: A versatile reagent in organic synthesis.
Diego Gamba-Sánchez.
Synlett, 2008, 1101-1102
DOI: 10.1055/s-2008-1066990 More...

Spotlight

It surveys the role of hydrogen peroxide in different organic transformations.

(2+2) -Photocycloaddition Reactions of Tetronic Acid Esters and Amides.
Jörg P. Hehn, Diego Gamba-Sánchez, Michael Kemmler, Martin Fleck, Birte Basler and Thorsten Bach.
Synthesis, 2010, 2308-2312.
DOI: 10.1055/s-0029-1218793 More...

PSP

Tetronic acid esteres and amides serve as starting materials for photocycloadditions. The typical conditions include irradiation at 254 nm and the use of ether or an alcohol as the solvent.

Synthesis of Modified Methyl Furanosides by Intramolecular oxa-Michael Reaction Followed by Pummerer Rearrangement.
Diego Gamba-Sanchez and Joëlle Prunet.
J.Org. Chem. 75, 2010, 3129-3132.
DOI: 10.1021/jo100241e More...

Note

A new method is described for the synthesis of ribofuranoses modified at the C3 and C5 positions. The key step is an intramolecular oxa-Michael reaction on a vinyl sulfoxide followed by Pummerer rearrangement.

Regio- and diastereoselective addition of allylic thioethers to aldehydes.
Diego Gamba-Sanchez, Raphaël Oriez, Joëlle Prunet.
Tetrahedron Lett., 50, 8, 2009, 883-885.
DOI: 10.1016/j.tetlet.2008.12.009 More...

Communication

A regioselective allylation and a regio- and diastereoselective crotylation of aldehydes with pyridin-2-yl sulfides were developed. The diastereoselective addition of crotyl phenyl sulfide to aldehydes was also optimzed.

Cyclisation/fluorination of nitrogen containing dienes in superacid HF–SbF5: a new route to 3- and 4-fluoropiperidines.
Emilie Vardelle, Diego Gamba-Sanchez, Agnès Martin-Mingot, Marie-Paule Jouannetaud, Sébastien Thibaudeau and Jérôme Marrot.
Chem. Commun, 12, 2008, 1473-1475.
DOI: 10.1039/B719309B More...

Communication

Various N,N-diallylic amines and amides were rapidly converted to fluorinated piperidines after a novel cyclisation/fluorination reaction in superacid HF–SbF5

About Us

Our aim is to develop new organic transformations and applying them in the total synthesis of natural products. The choice of the target molecules is made based on its biological activity; the synthesis of the natural occurring molecules is complemented with the synthesis of structural analogues oriented to improve their biological properties. 

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