Additions of allenyl/propargyl organometallic reagents to 4-oxoazetidine-2-carbaldehydes: novel palladium-catalyzed domino reactions in allenynes

Chemistry : a European Journal
Benito AlcaideCristina Aragoncillo

Abstract

Metal-mediated carbonyl allenylation and propargylation of 4-oxoazetidine-2-carbaldehydes were investigated in aqueous environment. Different propargyl bromide and metal promoters showed varied regio- and stereoselectivities on product formation. In addition, an unprecedented one-pot stereoselective synthesis of beta-chlorinated allylic alcohols, which can also be considered as functionalized allylsilanes, has been developed, which involves tin(IV) chloride-mediated reaction of propargyltrimethylsilane and 4-oxoazetidine-2-carbaldehydes. Some of the resulting coupling products were submitted to transition metal catalyzed reactions, such as the allenic Pauson-Khand and palladium-catalyzed reactions, leading to novel fused or bridged tricyclic beta-lactams. Remarkably, a novel domino process, namely the allene cyclization/intramolecular Heck reaction was found. A likely mechanism for the cascade reaction should involve an intramolecular cyclization on a (pi-allyl)palladium complex and a Heck-type reaction.

References

Jul 10, 1999·Amino Acids·C PalomoM Oiarbide
Oct 24, 2001·The Journal of Organic Chemistry·Benito AlcaideMiguel A. Sierra
Nov 1, 2001·Chemistry : a European Journal·I Macsári, K J Szabó
Dec 26, 2001·Chemical Reviews·R ZimmerF A Khan
Feb 19, 2002·Chemical Reviews·Ian FlemingDavid Walter
Aug 5, 1997·Chemical Reviews·Robert E. Babine, Steven L. Bender

❮ Previous
Next ❯

Citations

Dec 6, 2005·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Hiroaki Ohno
Nov 5, 2011·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Benito Alcaide, Pedro Almendros
Aug 1, 2007·Angewandte Chemie·Benito AlcaideTeresa Martínez del Campo
Oct 24, 2007·Chemistry : a European Journal·Benito AlcaideMaría C Redondo
Apr 4, 2008·Organic & Biomolecular Chemistry·Hiroyuki NakamuraJean-François Biellmann
Apr 19, 2008·Organic & Biomolecular Chemistry·Benito AlcaideM Rosario Torres
Jan 10, 2009·Chemistry : a European Journal·Benito AlcaideJosé L Marco-Contelles
Dec 1, 2005·Angewandte Chemie·Masahiro Inoue, Masahisa Nakada
Jun 17, 2006·Chemical Communications : Chem Comm·Benito AlcaideMaría C Redondo
Jun 10, 2011·Chemistry : a European Journal·Vanessa M MarxD Jean Burnell
Jan 23, 2004·Chemical Society Reviews·Jaime Blanco-UrgoitiJavier Pérez-Castells
Jan 31, 2012·Angewandte Chemie·Youqian DengJan-E Bäckvall
Aug 19, 2009·Chemistry, an Asian Journal·Benito AlcaideAlberto Rodríguez-Vicente
Aug 9, 2012·Chemical Communications : Chem Comm·Leleti Rajender Reddy
Feb 12, 2014·Chemical Society Reviews·S KitagakiC Mukai
Feb 7, 2014·Chemical Society Reviews·Jean Le Bras, Jacques Muzart
Jun 19, 2008·The Journal of Organic Chemistry·Julien BeignetLiam R Cox
Nov 1, 2012·Chemical Reviews·Zhi-Liang ShenTeck-Peng Loh
Jun 10, 2014·The Journal of Organic Chemistry·Benito AlcaideM Rosario Torres
Mar 5, 2015·Organic Letters·Michael Wegener, Stefan F Kirsch
Feb 15, 2003·The Journal of Organic Chemistry·Benito AlcaideMaría C Redondo

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.