Cyclopropanol ring opening

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

ACIE paper

Asymmetric Sn2 prime

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

ACIEE paper

Fluoride displacement via Sn2 prime

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.

ACIEE paper

Sn2′ – decarboxylation – Sn2′

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

European JOC paper

Water displaces an allylic chloride, asymmetrically

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

ACIEE paper

Thiophosphoric acid catalyzed hydroamination – ASYMMETRIC

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

Nature paper

Copper Catalyzed Sn2 prime

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.

 

JOC paper

DYKAT Sn2 Prime

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.

 

ACIEE paper

Mitsunobu Reaction in an Sn2 Prime Context

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

 

TL paper

Sn2 Prime Followed by SE2 Prime

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.

 

OL paper