1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes

Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles.

Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nuc...

The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions.

The Diels-Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3-butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, ...

Iridium–catalyzed 1,3–dipolar cycloadditions

1,3–Dipolar cycloaddition reactions (DCR) are atom–economic processes that permit the construction of heterocycles. Their enantioselective versions allow for the creation of up to four adjacent chiral centers in a concerted fashion. In particular, well–defined half–sandwich iridium (III) catalysts have been applied to the DCR between enals or methacrylonitrile with nitrones. Excellent yield and...

Access to functionalised silver(I) and gold(I) N-heterocyclic carbenes by [2 + 3] dipolar cycloadditions.

A new strategy was developed for the modification of silver(I) and gold(I) N-heterocyclic carbenes. Azido groups were grafted and used either by copper-catalysed azide-alkyne cycloaddition before metallation or by thermal and "strain-promoted" 1,3-dipolar cycloaddition after metallation to functionalise the metal-NHCs.

Theoretical study of 1, 3-dipolar cycloadditions of nitrone and fulminic acid with substituted ethylenes