Naturalproductman’s Blog

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Archive for the ‘Mechanistic’ Category

From a dithiane-vinyl chloride to furan

Posted by naturalproductman on April 19, 2016

Shouchu Tang and co-workers from Lanzhou University have reported in Organic Letters on an interesting transformation that undergoes an allene intermediate.

 

OL paper

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

Enyne metathesis – a mechanistic investigation

Posted by naturalproductman on April 14, 2016

Steven Diver and co-workers at SUNY Buffalo have reported in JACS on a mechanistic study of enyne metathesis using Hoveyda catalyst and Grubbs 2nd generation catalyst.

 

JACS paper

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

Olefin difluorination

Posted by naturalproductman on April 5, 2016

Eric Jacobsen and co-workers reported in JACS on a difluorination of an olefin. They accomplished this transformation by using mCPBA (1.1 equivalent), HF-pyridine (100 equivalents of HF), and an aryl iodide derivative (catalyst).

 

JACS paper

Posted in Hypervalent Iodine, Mechanistic, Methodology | Leave a Comment »

[4+2] with diazo esters

Posted by naturalproductman on February 8, 2016

Michael Doyle and co-workers at UT San Antonio have reported in JACS on the first Diels-Alder example involving a diazoester dienophile.

DOYLE jacs 2016

JACS paper

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

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 »

2 Reagents, 2 mechanisms, same product

Posted by naturalproductman on January 28, 2016

Srinivasan Chandrasekaran and colleague at the Indian Institute of Science have reported in Tetrahedron on a mechanistically interesting transformation involving a geminal aminooxygenation of a vinyl arene. Two different reaction conditions were identified: one with m-CPBA, the other with a hypervalent iodine reagent. The former underwent a deuterium shift on the gem-dideuterated-styrene starting material and the latter does not.

01.28.2016 naturalproductman.gif

Tetrahedron paper

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

JOC papers of interest 11/24/2015

Posted by naturalproductman on November 24, 2015

James White and co-workers reported on the synthesis of Huperzine A.

Christopher Marvin and co-workers from Hendrix College reported in JOC on the synthesis of tetrabenazine through a photoredox reaction to afford the piperidone moiety.

Young-Ger Suh and co-workers from Seoul National University reported on the synthesis of galiellalactone.

Ronaldo Pilli and co-workers from  Universidad Estadualde Campinas have reported on the synthesis of cryptomoscatone E3.

Scott Denmark and colleague reported on an asymmetrice 2,3-Wittig rearrangement.

JOC 11.24.2015 FKY

Posted in Alkaloids, Light Mediated, Mechanistic, Methodology, Sigmatropic Rearrangements, Total Synthesis | Leave a Comment »

From gene clusters to biosynthesis of natural products

Posted by naturalproductman on October 16, 2015

Leadlay (University of Cambridge) and Sun (Wuhan University) and co-workers have reported in Chemical Science on thiotetronate biosynthesis.

gene

Chemical Science paper

Posted in Biosynthesis, Mechanistic, Thiotetronate | Leave a Comment »

Evans enolate in solution

Posted by naturalproductman on October 5, 2015

David Collum and colleague have reported in JACS on the solution structure of an Evans enolate.
Evans

JACS paper

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

Mechanistic study of the asymmetric Nazarov cyclization

Posted by naturalproductman on October 1, 2015

Kendall Houk and co-workers reported in JACS on a mechanistic investigation on a reaction discovered by Tius: the asymmetric Nazarov cyclization catalyzed by a thiourea-primary amine catalyst.

DFT

JACS paper

Posted in Computational, DFT, Mechanistic, Named Reactions, Nazarov cyclization | Leave a Comment »

 
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