Treatment of the diol 6 with KH and 18-C-6 at room temperature gives the cyclopentenone 7 in good yields. Mechanistic analysis reveals that this is the first case of an anionic oxy retro-ene reaction followed by a tandem intramolecular aldol condensation. Reaction: see text.

The C-C bond fragmentation of carbocycles has been developed as a new method for the divergent synthesis of dendrimers. The scope of this reaction was examined with the preparation of six first generation dendrimers from structurally diverse and readily available fragmentation precursors. By pairing the fragmentation with a thio-Michael reaction, the preparation of a [G4]-ene(24) dendrimer has ...

Homopolymer and block copolymer bearing carbohydrate side chain functionality were obtained by grafting glucothiose onto alkene functional scaffolds via a thiol-ene click reaction and the resulting copolymer was used to form thermo-responsive micelles as a potential drug carrier.

A novel three-component reaction has been developed to assemble biologically and pharmaceutically important tetracyclic fused imidazo[1,2-a]pyridines in a one-pot fashion utilizing readily available 2-aminopyridines, isatins and isocyanides. The three-component coupling proceeds through the Groebke-Blackburn-Bienaymé reaction followed by a retro-aza-ene reaction and subsequent nucleophilic reac...

Glycosyl thiols may be accessed from the corresponding reducing sugars in water without recourse to any sugar projecting groups by way of a DMC mediated reaction with thioacetic acid in the presence of base, and hydrolysis of the anomeric thioacetate. Glycosyl thiols produced by this method may be used to access glycoconjugates, such as glycopeptides by use of the thiol-ene click reaction.

An efficient relay catalytic process involving Au(i)/Brønsted acid to access various polysubstituted cyclopentannulated indoles from easily accessible 1-(2-aminophenyl)prop-2-ynols and readily available 1,3-dicarbonyls has been developed. In an unprecedented event, the intermediate 2-indolylmethyl cations undergo the cation-Ene reaction with various 1,3-dicarbonyls followed by an intramolecular...

The ring-opening of N-tosylaziridines with various acid anhydrides catalyzed by 5 mol % of 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) afforded the corresponding β-amino esters in excellent yields under mild reaction conditions. Polymer-supported catalyst, PS-TBD also acts as a good catalyst for this reaction. PS-TBD was easily recovered and reused with minimal loss of activity.

[Structure: see text] Thermal treatment of 1,6-fullerenynes bearing an alkyl group on the terminal carbon of the alkyne moiety leads quantitatively to new allenes through a reaction mechanism involving an intramolecular ene process. This reaction outcome is in contrast to that recently found for free terminal alkynes which form cyclobutene derivatives through a [2+2] cyclization mechanism.

The key steps in the synthesis of clavulactone are formation of an enantiopure cyclopentane precursor by epoxide rearrangement and intramolecular carbonyl-ene reaction, construction of the 3,4-dihydro-2H-pyran ring by intermolecular hetero-Diels-Alder reaction, closure of the eleven-membered ring, and finally generation of the lactone functionality by chemoselective allylic C(sp(3))-H oxidation.

The substitution reaction of allylic derivatives (acetate, carbonate, and chloride) with tinacetylene proceeded in the presence of palladium as a catalyst to give a product having a 1-ene-4-yne system.