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Archive for the ‘Sn2 prime’ Category

Nucleophilic substitution to kick out leaving group on the allylic position

Cyclopropanol ring opening

Posted by naturalproductman on August 22, 2012

Jin Kun Cha and co-workers at Wayne State University have reported in ACIE on a ring opening of cyclopropanol using stoichiometric diethyl zinc.

sn2 prime

ACIE paper

Posted in Cascade Reactions, Methodology, Ring Opening, Sn2 prime, Transition Metal, Zinc | Leave a Comment »

Asymmetric Sn2 prime

Posted by naturalproductman on December 9, 2011

Alexandre Alexakis and colleague at the University of Geneva have reported in ACIEE on an asymmetric SN2 prime reaction using an enyne chloride substrate.

enyne

ACIEE paper

Posted in Asymmetric, Copper, Methodology, Sn2 prime, Transition Metal | Leave a Comment »

Fluoride displacement via Sn2 prime

Posted by naturalproductman on September 28, 2011

Jean-Francois Paquin and co-workers from the Universite Laval have reported in ACIEE on an Sn2 prime displacement of a fluoride group starting with an allylic bis-fluoride substrate to afford a vinyl fluoride.

sn2 prime

ACIEE paper

Posted in Cascade Reactions, Methodology, Sn2 prime | Leave a Comment »

Sn2′ – decarboxylation – Sn2′

Posted by naturalproductman on June 5, 2011

Jacques Rouden and co-workers from CNRS have published in European JOC on a metal free decarboxylative rearrangement of a beta-ketoester.

decarboxylation

European JOC paper

Posted in Cascade Reactions, Mechanistic, Methodology, Organocatalytic, Sn2 prime | Leave a Comment »

Water displaces an allylic chloride, asymmetrically

Posted by naturalproductman on April 22, 2011

Kiyotaka Onitsuka and colleague at Osaka University have reported in ACIEE on a ruthenium catalyzed Sn2 prime reaction where water displaces a chloride.
ruthenium

ACIEE paper

Posted in Asymmetric, Conjugate Additions, Methodology, Ruthenium, Sn2 prime, Transition Metal | Leave a Comment »

Thiophosphoric acid catalyzed hydroamination – ASYMMETRIC

Posted by naturalproductman on February 10, 2011

Dean “da Man” Toste and co-workers at Berkeley have published in Nature on a thiophosphoric acid catalyzed intramolecular hydroamination of a diene.

phosphoric acid

Nature paper

Posted in Asymmetric, Cascade Reactions, Methodology, Organocatalytic, Sn2 prime | Leave a Comment »

Copper Catalyzed Sn2 prime

Posted by naturalproductman on January 31, 2011

Kiyoshi Tomioka and co-workers at Kyoto University have reported in the Journal of Organic Chemistry on a copper N-heterocyclic carbene complex that catalyzes an Sn2 prime reaction.

Sn2 prime

 

JOC paper

Posted in Carbene, Copper, Methodology, Sn2 prime, Transition Metal | Leave a Comment »

DYKAT Sn2 Prime

Posted by naturalproductman on January 24, 2011

Alexandre Alexakis and co-worker at the University of Geneva have published in ACIEE on a copper catalyzed Sn2 prime reaction that results in the formation of a mixture of Z and E isomers.  The neat thing about this transformation is that the starting material is a racemic allylic chloride which through the addition of the alkyl metal results in a single enantiomer but mixture of E and Z isomers.

asymmetric Sn2 prime

 

ACIEE paper

Posted in Asymmetric, Copper, Methodology, Sn2 prime, Transition Metal | Leave a Comment »

Mitsunobu Reaction in an Sn2 Prime Context

Posted by naturalproductman on December 20, 2010

Kazuhiko Sakaguchi and co-workers at Osaka City University have published in Tetrahedron Letters on a Mitsunobu type anti-Sn2 prime reaction.

sn2 prime

 

TL paper

Posted in Cascade Reactions, Mechanistic, Methodology, Mitsunobu, Named Reactions, Sn2 prime | Leave a Comment »

Sn2 Prime Followed by SE2 Prime

Posted by naturalproductman on November 19, 2010

Tamotsu Takahashi and co-workers at Hokkaido University have published in Organic Letters on a palladium catalyzed Sn2 prime reaction followed by a desilylative SE2 prime reaction.

sn2 prime

 

OL paper

Posted in Asymmetric, Cascade Reactions, Methodology, Palladium, Sn2 prime, Transition Metal | Leave a Comment »

 
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