By A. C. Knipe
The one publication sequence to summarize the newest development on natural response mechanisms, natural response Mechanisms, 2011 surveys the advance in knowing of the most sessions of natural response mechanisms suggested within the basic clinical literature in 2011. The forty seventh annual quantity during this hugely winning sequence highlights mechanisms of stereo-specific reactions. studies are compiled by way of a crew of skilled editors and authors, permitting complicated undergraduates, graduate scholars, postdocs, and chemists to depend upon the volumes carrying on with caliber of choice and presentation.
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Extra resources for Organic Reaction Mechanisms 2011: An annual survey covering the literature dated January to December 2011
Example text
267 o-Chloroaromatic α-ketoamides (81) undergo an intramolecular nucleophilic addition to give 3-hydroxyindoles (82), using dimethylzinc as reductant, and catalysis by NiCl2 (PCy3 )2 . 268 The specific roles of each metal of nickel/chromium catalysts of Nozaki-HiyamaKishi coupling of vinyl halides and aldehydes have been studied by UV–visible spectroscopy, electrochemistry, and spectroelectrochemical methods. Chromium(II) chloride does not react with the vinyl halide but converts nickel(II) to nickel(I) species, which does.
Double cyclization gives a 2,2 -bifuran. 280 Aryl trifluoromethyl ketones have been alkynylated in high ee using readily available chiral cinchona alkaloids that afford either propargylic tertiary alcohol product ee 30 Organic Reaction Mechanisms 2011 F 3C O O NaC CH F 3C HO Δ , then H+ CF3 OH O O Ar Ar Ar (85) (86) enantiomer. The reaction is promoted by titanium(IV) and requires a dialkylzinc, but also needs a metal fluoride additive. 287 Aldehydes have been propargylated in up to 99% yield and 92% ee by allenylzinc reagents, generated in situ from the action of diethylzinc on iodoallene (or 3iodopropyne), with a bulky diarylprolinol catalyst.
A successive aldol–aldol-Tishchenko version gave a triol (79) with five contiguous centres. 249 Several organothorium complexes catalyse Tishchenko coupling or dimerization of aldehydes (RCHO) to esters (RCO2 CH2 R), a disproportionation reaction with 100% atom efficiency. 253 For more references to Aldols, see section titled ‘Reactions of Glucosides’. 257 A Ti/Pd bimetallic system catalyses allylation of carbonyl compounds, using allyl carbonates, and is particularly useful for ketones that are reluctant participants in many allylation protocols.