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Archive for the ‘Sigmatropic Rearrangements’ Category

Cope rearrangement

Posted by naturalproductman on August 23, 2016

James Gleason and colleague at McGill University have reported in ACIE on an organocatalytic Cope rearrangement.

 

ACIE paper

Posted in Cascade Reactions, Methodology, Organocatalytic, Sigmatropic Rearrangements | 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 »

Sigmatropic rearrangement cascade

Posted by naturalproductman on October 28, 2015

Here’s another example of the student who published a single author paper. Yang Yang at MIT from Buchwald’s lab reported in ACIE on a very cool sigmatropic rearrangement.
sigmatropic
ACIE paper

Posted in Cascade Reactions, Copper, Sigmatropic Rearrangements, Transition Metal | Leave a Comment »

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 »

Reverse Claisen cascade

Posted by naturalproductman on April 16, 2015

Yongjia Shang and co-workers from Anhui Normal University have reported in JOC on an interesting iron catalyzed cascade reaction.

JOC paper

Posted in Cascade Reactions, Claisen rearrangement, Iron, Methodology, Sigmatropic Rearrangements, Transition Metal | Leave a Comment »

Copper catalyzed reduction to form indolynes

Posted by naturalproductman on April 12, 2015

Stephen Buchwald and colleague have reported in JACS on a copper catalyzed C-C bond formation to make indolynes. This is a reduction reaction and they use diethoxymethylsilane (DEMS) to serve as the reductant.

copper

JACS paper

Posted in Copper, Methodology, Sigmatropic Rearrangements, Transition Metal | 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 »

Limazepine E synthesis

Posted by naturalproductman on August 30, 2013

Ronalds Zemribo and colleague at the Latvian Institute of Organic Chemistry have reported in Org Lett on a an Ireland-Claisen rearrangement approach to synthesizing limazepine E and barmumycin.

limazepine E

OL paper

Posted in Alkaloids, Cascade Reactions, Ireland-Claisen rearrangement, Methodology, Named Reactions, Pericyclic reactions, Sigmatropic Rearrangements | 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 »

Asymmetric allylic amination

Posted by naturalproductman on October 29, 2012

Uttam Tambar and colleague at UT Southwestern have reported in JACS on a process involving the allylic amination of terminal olefins using a benzene using a benzenesulfonyl sulfurdiimide reagent.

amination

JACS paper

Posted in Asymmetric, Methodology, Sigmatropic Rearrangements | Leave a Comment »

 
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