Current Organic Chemistry - Volume 15, Issue 14, 2011

Polar Organometallic compounds, a term coined by professor Manfred Schlosser, became reagents of choice to ascertain a high degree of structural diversity with applications in organic synthesis, material science and industrial applications in pharmaceutical and agrochemical fields. The subtle interplay between a metal (the alkali metals, the alkaline earth metals and even organozinc compounds) with a carbon backb Read More

Trimethylsilylmethyllithium (TMSCH2Li) is well-known as a nucleophilic reagent in methylation and methylenation reactions but its application in deprotonation or halogen-metal exchange has been underexploited to date. The present review covers new applications of TMSCH2Li and TMSCH2Li-LiDMAE (LiDMAE=Lithium 2-dimethylamino ethoxide) in selective metallation of pyridine derivatives focusing on the design of Read More

Efficient deprotonative cadmiation reactions of functionalized aromatics including heterocycles have been realized using TMP-cadmiate, (TMP)3CdLi (TMP = 2,2,6,6-tetramethylpiperidino). The reagent is compatible with reactive functional groups (amide, ester, nitrile and even ketone functions), heavy halogens (Br, I), five-membered aromatic heterocycles (furan, thiophene, oxazole, thiazole, and pyrrole derivatives) and even aro Read More

The recent publications on the topic of the preparation of organolithium reagents by non-deprotonating methodologies and starting from non-halogenated substrates have been covered in the present revision. In this second part, transmetallation processes, mainly tin-lithium exchange, and addition to multiple bonds have been considered. Moreover, other procedures, such as carbon-carbon bond scission and the Shapir Read More

The advice of professor Dieter Seebach “Thinking of polar organometallics compounds as carbanions is an impoverishment rather that a simplification” (ISCC, Durham 1984), perfectly fits the statement of professor Manfred Schlosser, who coined the term polar organometallic”, according which no difference in reactivity patterns of organometallic reagents can be rationalized without taking into account the meta Read More

The Meyers reaction, i.e. the nucleophilic aromatic substitution reaction between aryloxazolines with organolithium and organomagnesium reagents is a very efficient and reliable method for the formation of new carbon-carbon and carbon-heteroatom bonds. The aim of this review is to present a general overview of this reaction in chiral and racemic form, emphasizing its scope and limitations. The literature is covered since 1994.

In this review, the use of molecular iodine as a catalyst in the synthesis of heterocyclic compounds is presented and reviewed. In recent years, the use of molecular iodine in organic chemistry has received considerable attention because the chemical (a) is inexpensive and readily available, (b) is less toxic than alternatives, (c) has an easy workup method, and (d) is a moisture-stable, mild Lewis acid. Many of the reactions using i Read More

This review deals with synthesis of thiophosphinic acids. Some of these reactions have been applied successfully to the synthesis of chemically or biologically interesting compounds. The main purpose of this review is to cover the literature on thiophosphinic acids from the first report up to date since such compounds have not been previously reviewed.

Pyrazolo[1,5-a]pyridines have become subject to growing interest by both synthetic and medicinal chemists, and as such new and simple methods for their synthesis are becoming increasingly more important. They exhibit reactivity which permits substitution at various positions, allowing many diverse chemical structures to be made. This review briefly discusses the medicinal uses of pyrazolo[1,5-a]pyridines, it outlines the synth Read More

Herein we give a brief account of the efforts our group made in recent years to discover novel enzymes and utilize them by bioprocess engineering techniques for stereoselective synthesis of various enantiomerically pure chiral chemicals with high value in a greener manner. Included are discussions on oxidoreductases, expoxide hydrolases and glucosidases in whole cells or isolated form from microorganisms or plants.

Microwave-assisted [2+2] cycloadditions of (E)-3-dimethylamino-1-substituted prop-2-en-1-ones, prepared from carbocyclic, aromatic and heteroaromatic methyl ketones, ethyl acetate, diethyl malonate, ethyl methoxyacetate, methyl phenoxyacetate and dietyl acetylenedicarboxylate give substituted dimethyl 2-[(dimethylamino)methylene]succinates.