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Archive for the ‘Isotope effects’ Category

The enamine is formed through an oxazolidinone intermediate

Posted by naturalproductman on February 4, 2016

When I think of organocatalysis, I usually think of a carbonyl compound forming an enamine intermediate, which in turn attacks an electrophile. The enamine is usually formed when the carbonyl compound reacts with a proline-derived catalyst. By using Gaussian and experimental KIE calculations, Matthew Vetticatt and co-workers at Binghamton University reported in JACS on the way that the enamine compound is formed: through an oxazolidinone intermediate.

oxazolidinone

JACS paper

 

A review article on determining the transition state structures based on KIEs.

Posted in Computational, Isotope effects, Mechanistic | Leave a Comment »

Syn-elimination

Posted by naturalproductman on May 14, 2014

Cristina de Meo and co-workers from Southern Illinois University reported in Organic Letters on a thiosialoside elimination of a thiophenol group, occuring by syn-elimination.

syn

OL paper

Posted in Half-chair, Isotope effects, Mechanistic | 1 Comment »

Half chair transition state

Posted by naturalproductman on February 17, 2012

Andrew Bennet and co-workers from Simon Fraser University have reported in JACS on a transition state study of a sialidase enzyme.

sialidase

JACS paper

Posted in Enzymes, Glucoside, Isotope effects, Mechanistic, Methodology, Proteins | Leave a Comment »

Ru-catalyzed hydroamidation

Posted by naturalproductman on April 26, 2011

Lukas Goossen and co-workers at TU Kaiserslautern have reported in JACS on a mechanistic investigation of a ruthenium catalyzed hydroamidation reaction of an alkyne.

ruthenium

JACS paper

Posted in Cascade Reactions, Isotope effects, Mechanistic, Methodology, Ruthenium, Transition Metal | Leave a Comment »

 
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