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Archive for the ‘Sigmatropic Rearrangements’ Category

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 »

Double benzylic rearrangement

Posted by naturalproductman on August 16, 2012

Angel Montana and co-workers at the University of Barcelona have reported in Tetrahedron on a double benzylic rearrangement.

benzylic

Tetrahedron paper

Posted in Cascade Reactions, Curtin rearrangement, Mechanistic, Methodology, Named Reactions, Sigmatropic Rearrangements | Leave a Comment »

 
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