Enantiospecific Suzuki-Miyaura

Michinori Suginome and co-workers at Kyoto University have published in JACS on the enantiospecificity of a Suzuki-Miyaura reaction and they show that inversion or retention can occur depending on the additive.

JACS paper

Pyrrole access

Manojit Pal and co-workers from the University of Hyderabad have reported in Chem Comm on a multi-component reaction to make substituted pyrroles.

Chem Comm paper

Haouamine B Progress

Yoshiki Morimoto and co-workers from Osaka City University have published in Chemical Communications on their progress towards haouamine B.  Phil Baran and co-worker have published on a synthesis of haouamine A – however, haouamine B, which differs from the A form by a hydroxy group in one of the aryl rings (the one fused to the five membered ring), is less stable than A and has not been synthesized yet.

Chem Comm paper

Didemnaketal Synthesis

Haruhiko Fuwa and co-workers from Tohoku University have published in Organic Letters on a synthesis of didemnaketal which has an IC50 value of 1 micromolar against HIV-1 protease.  The spiroketal unit was accessed from a PPTS catalyzed condensation of an alcohol and a dihydropyran.

 

OL paper

Suzuki-Miyaura with Aryltriazenes

Meiming Luo and co-workers from Sichuan University have published in the Beilstein Journal of Organic Chemistry on a Suzuki-Miyaura reaction that involves the use of a triazene compound, which couples with an arylboronic acid.

Beilstein JOC paper

Indene Synthesis

Mark Lautens and co-worker at the University of Toronto have published in Organic Letters on the use of a gem-dibromoalkene to form an indene ring and a new C-C bond via an intermolecular Suzuki/Heck reaction.  Usually we see alkynes as precursors to these transition metal catalyzed indene formations, but this dibromo-olefin is another approach.

OL paper

Boron Enolate from Alkyne

Tom Sheppard and co-workers from the University College in London have recently reported in JACS on an unconventional way to form boron enolates from alkynes – it basically looks like the addition of the -OH group accross the alkyne for a 6-endo-dig cyclization.

JACS paper

OL paper

Regioselective Suzuki-Miyaura

Peter Langer and co-workers at the Universitat Rostock have recently published in Synlett on a regioselective Suzuki-Miyaura reaction that selectively couples a boronic acid to a specific triflate on an aryl ring.  Their explanation had to do with the electronics.

Synlett paper

Tandem Oxidation-Wittig

Richard Taylor and co-workers at the University of York have recently published in Synlett on a tandem approach to synthesize dibromo-beta-substituted enone from an alpha hydroxy ketone.   Hydrazine was condensed with the carbonyl and a Suzuki-Miyaura cross coupling followed to form a pyrazole ring.

Synlett paper

A Palladium Cascade

Antonio Mourino and co-workers at the Universidad de Santiago de Compostela y Unidad Asociada al CSIC in Spain have recently published in Chemistry – A European Journal on a cascade reaction catalyzed by palladium – the reaction involves a cyclization of an alkynyl enol triflate followed by a Suzuki-Miyaura coupling with the vinyl palladium intermediate.

Chemistry – A European Journal paper