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Archive for the ‘Mechanistic’ Category

Newman-Kwart reaction mechanism

Posted by naturalproductman on July 13, 2015

Hafize Ozcan and co-workers from Trakya University in Turkey have reported in Tetrahedron on an interesting mechanistic investigation of the Newman-Kwart reaction.

Newman-Kwart

Tetrahedron paper

Posted in Cascade Reactions, Computational, DFT, Electrocyclization, Mechanistic, Methodology, Named Reactions, Newman-Kwart, Sigmatropic Rearrangements | Leave a Comment »

α-Ketol rearrangement

Posted by naturalproductman on June 9, 2015

Ulrich Koert and co-workers from Philipps-University Marburg have reported in Organic Letters on an alpha-ketol rearrangment.They heat the reaction in a sealed tube to 70 degrees and the solvent is in DCM – with 2.5 mol equivalents of BF3 etherate, sounds a bit harsh – but nonetheless an interesting sigmatropic rearrangement.

 
ketol
OL paper

Posted in Cascade Reactions, Mechanistic, Methodology | Leave a Comment »

Sufur ylide chemistry – intramolecular cyclopropanation

Posted by naturalproductman on May 28, 2015

Nuno Maulide and co-workers from the University of Vienna have reported in JOC on an intramolecular cyclopropanation from a sulfur slide precursor and what follows is a nice mechanistic investigation.

sulfur

JOC paper

Posted in Computational, DFT, Gold, Mechanistic, Methodology, Transition Metal | Leave a Comment »

Domino acylation Diels-Alder

Posted by naturalproductman on May 2, 2015

Jeffrey Aube (University of Kansas) and Dean Tantillo (UC Davis) have teamed up to study the mechanism of a domino acylation-Diels Alder reaction.

domino

OL paper

Posted in DFT, Diels-Alder, Mechanistic, Methodology, Named Reactions | Leave a Comment »

Terpene cyclization involving carbons switching

Posted by naturalproductman on March 5, 2015

Tomohisa Kuzuyama and co-workers at the University of Tokyo have reported in ACIE on an mechanistically interesting terpene cyclization involving two carbons switching.

terpene

ACIE paper

Posted in Biosynthesis, Enzymes, Mechanistic, Proteins | Leave a Comment »

Sigmatropic rearrangements

Posted by naturalproductman on January 18, 2015

Matthew Cook and co-workers from Queen’s University Belfast in the UK have reported in JOC on some interesting sigmatropic reactions, depending on the base used, an isomerization Claisen occurs or a [2,3]-Wittig-anionic oxy-Cope rearrangement occurs.
rearrangement
JOC paper

Posted in Mechanistic, Methodology, Pericyclic reactions, Sigmatropic Rearrangements | Leave a Comment »

Alkyl halides from aryl halides

Posted by naturalproductman on November 8, 2014

Zhenfeng Xi and co-workers from SIOC have reported in ACIE on the transfer of a halogen from an aryl group to an alkyl group.

reductive elimination

ACIE paper

Posted in Mechanistic, Methodology, Palladium, Transition Metal | Leave a Comment »

Pd pi-allyl

Posted by naturalproductman on November 8, 2014

Shu-Li You and co-workers at SIOC have reported in JACS on some mechanistic studies of a Pd pi-allyl chemistry.

pi allyl

JACS paper

Posted in Asymmetric, Mechanistic, Methodology, Named Reactions, Palladium, Transition Metal, Tsuji-Trost | Leave a Comment »

Breaking benzene

Posted by naturalproductman on August 28, 2014

Petr Beier and co-workers from the Academy of the Sciences of the Czech Republic have reported in JOC on an interesting reaction involving hydrogen peroxide, and an SF5-phenol to afford a muconolactone derivative.

BV
JOC paper

Posted in Cascade Reactions, Mechanistic, Methodology, Named Reactions | Leave a Comment »

Rearrange to more complexity

Posted by naturalproductman on July 27, 2014

Paul Hergenrother and co-workers from UIUC have reported in ACIE on an interesting rearrangement to form fenestrane ring systems.

cyclopropane

ACIE paper

Posted in Antibiotics, Cascade Reactions, Mechanistic, Methodology | Leave a Comment »

 
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