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Archive for the ‘Mechanistic’ Category

Oxazoles to pyridines

Posted by naturalproductman on May 7, 2013

Pierre Yves-Renard and co-workers from CNRS have reported in Organic Letters on an interesting synthesis of pyridines.

pyridines

OL paper

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

Endoperoxide rearrangement

Posted by naturalproductman on May 7, 2013

Ihsan Erden and co-workers at SFSU have reported in Tetrahedron on an endoperoxide rearrangement.

rearrangement

Tetrahedron paper

Posted in Mechanistic, Methodology | Leave a Comment »

Asymmetric epoxidation

Posted by naturalproductman on April 19, 2013

Benjamin List and co-workers have reported in JACS on their studies of cinchona alkaloid catalyzed asymmetric epoxidation of activated olefins.

cinchona

JACS paper

Posted in Asymmetric, Computational, DFT, ESI, Mass Spectrometry, Mechanistic, Methodology, Organocatalytic | Leave a Comment »

Garuganin and garugamblin syntheses

Posted by naturalproductman on March 20, 2013

Chris Beaudry and co-workers at Oregon State have reported in JOC on some syntheses of diaryl heptanoids.

heptanoids

JOC paper

Posted in Asymmetric, Heptanoids, Mechanistic, Methodology, Structural Reassignment, Total Synthesis | Leave a Comment »

Iron catalyzed [2+2]

Posted by naturalproductman on March 15, 2013

Paul Chirik and co-workers from Princeton have reported in JACS on a mechanistic study of an iron catalyzed [2+2].

iron

JACS paper

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

ATR-FTIR-UV/Vis monitoring of a reaction

Posted by naturalproductman on March 13, 2013

Ursula Bentrup and co-workers at Universitat Rostock in Germany have reported in Tetrahedron on an interesting setup to monitor a reaction.

monitor

Tetrahedron paper

Posted in Mechanistic, Methodology, New Setups, Titanium, Transition Metal | Leave a Comment »

Alkynoates and allylic ethers

Posted by naturalproductman on February 27, 2013

Young Ho Rhee and co-workers from Pohang University of Science and Technology have reported in Org Lett on a gold catalyzed coupling of an alkynoate and allylic ether.

ether

OL paper

Posted in Cascade Reactions, Gold, Mechanistic, Methodology, Sigmatropic Rearrangements, Transition Metal | Leave a Comment »

Oxazole cascade transformation

Posted by naturalproductman on November 12, 2012

Stephen Habay and co-workers from Salisbury University in Maryland have published in JOC on a transformation of oxazoles to octahydroindoles.

cyclohexanone
JOC paper

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

C-C bond breaking mechanism

Posted by naturalproductman on November 8, 2012

Here’s an interesting paper where the authors used 18O2 to label one of the oxygens found in the product to investigate the mechanism. Now I’m going to be a little bit critical here but in the supporting information they put the 18O-label on the carbonyl oxygen but in the manuscript they don’t know if it is on the O-benzyl of the ester or the carbonyl oxygen. Moreover the abstract figure shows that the 18O is on the carbonyl oxygen but they really don’t know. It’s a bit deceiving in the paper because it kind of sounds like they determined it through GC-MS but in the supporting information I could not find the GC-MS trace. I guess there is a limitation in analytical technology to determine the position of the 18O. But still it is not clear from the paper that they don’t know which position the 18-oxygen is.

O

ACIE paper

Posted in C-C Bond Breaking, Cascade Reactions, Mechanistic, Methodology | Leave a Comment »

Rhodium catalyzed reaction

Posted by naturalproductman on November 6, 2012

P. Andrew Evans (University of Liverpool) and Mu-Hyun Baik (Indiana University) and co-workers have published in JACS on a mechanistic investigation of a rhodium catalyzed [3+2+1] cyclization. The Los Alamos LACVP basis set was used to represent rhodium.

rhodium

JACS paper

Posted in Computational, DFT, Mechanistic, Methodology, Rhodium, Ring forming, Silver, Transition Metal | Leave a Comment »

 
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