Naturalproductman’s Blog

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Archive for April, 2010

Nickel Catalyzed Amino-Arylation

Posted by naturalproductman on April 30, 2010

Adding aryl groups across alkynes seems to be a developing chemical transformation in the field.  Nicolas Guimond and co-workers at the University of Ottawa have recently reported in JACS on a C-N bond addition across an alkyne.

C-N

Posted in Cascade Reactions, Methodology, Nickel, Ring forming, Transition Metal | Leave a Comment »

Chirality Transfer

Posted by naturalproductman on April 30, 2010

Norbert De Kimpe and co-workers from Ghent University have recently reported in Chemical Communications on the reduction of chiral N-(tertbutanesulfinyl)ketimines with chlorides to yield chiral pyrrolidines upon reduction with LiBEt3H.

chirality transfer

Chem Comm paper

Posted in Asymmetric, Cascade Reactions, Methodology, Ring forming | Leave a Comment »

Nickel Catalyzed C-C Bond Cleavage

Posted by naturalproductman on April 30, 2010

Koichiro Oshima and co-workers from Kyoto University have recently reported in Organic Letters on a Ni-catalyzed C-C bond cleavage.

C-C Bond Cleavage
OL paper

Posted in C-C Bond Breaking, Methodology, Nickel, Transition Metal | Leave a Comment »

TIPCARM

Posted by naturalproductman on April 30, 2010

James White and co-workers have recently reported in JOC on a [2+2] photocycloaddition followed by a retro-Mannich cascade reaction (TIPCARM), which further undergoes another retro-Mannich reaction and a rearrangement to yield a spirocycle.

retro-Mannich

JOC paper

Posted in Cascade Reactions, Cycloaddition, Light Mediated, Methodology, Named Reactions, Pericyclic reactions, retro-Mannich | Leave a Comment »

Nickel’s C-H Activation

Posted by naturalproductman on April 30, 2010

Timothy Jamison and co-worker have recently reported in JACS on a nickel catalyzed allylic substitution of a mono-substituted alkene.

Ni-C-H Activation

JACS paper

Posted in C-H activation, Methodology, Nickel, Transition Metal | Leave a Comment »

Ugi-Approach for 4,4-Disubstituted Piperidines

Posted by naturalproductman on April 29, 2010

Guillaume Laconde and co-workers at INSERM have recently reported in Tetrahedron Letters on an Ugi reaction to synthesize 4-aminopiperidine-4-carboxylic acids.

ugi

Tetraheron Letters paper

Posted in Cascade Reactions, Methodology, Multi-Component Coupling, Named Reactions, Ugi | Leave a Comment »

Cyclohexyne

Posted by naturalproductman on April 29, 2010

Erick Carreira and co-workers have used cyclohexyne to cleave a C-C bond and expand a ring system.  A hypervalent iodine was used to generate the strained alkyne.

cyclohexyne

ACIEE paper

Posted in C-C Bond Breaking, Cascade Reactions, Cycloaddition, Electrocyclization, Hypervalent Iodine, Methodology, Pericyclic reactions | Leave a Comment »

Ullmann Reaction for Vinyl Enol Ethers

Posted by naturalproductman on April 29, 2010

Craig Merlic and co-worker at UCLA have recently reported in Organic Letters on an Ullmann reaction from a vinyl boron substrate to couple to the oxygen of an allylic alcohol.  The yield was optimized in the presence of a terminal alkyne, which was used as a ligand for copper.

ullmann
OL paper

Posted in Copper, cross coupling, Methodology, Transition Metal, Ullmann | Leave a Comment »

Pd-Catalyzed Spirocyclization

Posted by naturalproductman on April 28, 2010

Jieping Zhu and co-workers from CNRS have recently reported in Chemistry a European Journal on a spirocyclization process that forms two rings in one reaction with the use of a palladium catalyst.  One of the steps involves an aminopalladation to make the pyrrolidine-unit.

spirocyclization


Chemistry a European Journal paper

Posted in Cascade Reactions, Mechanistic, Methodology, Palladium, Spirocycles, Transition Metal | Leave a Comment »

Allene Times Two

Posted by naturalproductman on April 28, 2010

Benito Alcaide and co-workers (CSIC and University of Oxford) have recently reported in Chemistry – a European Journal on a cross coupling cyclization reaction between two different allene compounds in the presence of a palladium catalyst.

allene

Chemistry a European Journal paper

Posted in Allenes, Cascade Reactions, cross coupling, Methodology, Palladium, Transition Metal | Leave a Comment »

 
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