Dirk De Smaele

Sonochemical cleavage of 2-(bromomethyl)aziridines by a zinc–copper couple

1-Alkyl- and 1-arylmethyl-2-(bromomethyl)aziridines are readily cleaved by the sonochemical zinc–copper couple in aqueous methanol at room temp. to afford allylamines.

SYNTHESIS OF PYRROLIZIDINES BY CASCADE REACTIONS OF N-ALKENYLAZIRIDINYLMETHYL RADICALS

Abstract Pyrrolizidines were synthesized in a one-step-reaction from 2-(bromomethyl)aziridines via a cascade of radical reactions involving aziridinylmethyl radicals, N-allylaminyl radicals and carbon-centered pyrrolidinyl radicals.

SYNTHESIS OF 3-ALKENYLAMINES, 4-ALKENYLAMINES AND 3-ALLENYLAMINES VIA A TRANSAMINATION PROCEDURE

Abstract 3-Alkenylamines, 4-alkenylamines and 3-allenylamines were synthesized conveniently by potassium t-butoxide induced transamination of α-vinylaldimines, α-allylaldimines or α-allenylaldimines followed by hydrolysis with aqueous oxalic acid.

Synthesis of aziridines and azetidines from N-(ω-haloalkyl) imines

Abstract N-(2-Haloalkyl) and N-(3-haloalkyl) imines are convenient substrates for the synthesis of aziridines and azetidines via a two-step process involving nucleophile induced addition at the imino bond followed by intramolecular nucleophilic substitution.

A convenient synthesis of 3-alkoxyazetidines

Abstract N-(Alkylidene or arylidene)-2-substituted-2-propenylamines were regiospecifically functionalized into novel N-(alkylidene or arylidene)-2-alkoxy-3-bromo-2-substituted-propylamines, which were proven to be excellent sources for 3-alkoxyazetidines through sodium borohydride reduction of the imino bond and subsequent intramolecular nucleophilic substitution.

A new entry towards the synthesis of 1-substituted 3-azetidinones

The synthesis of 1-substituted 3-azetidinones, starting from readily accessible N-(alkylidene)- or N-(arylidene)-2,2,3-tribromopropylamines, is disclosed.

Synthesis of functionalized pyrrolidines from N-(benzylidene)- and N(alkylidene)-homoallylamines

N-(Benzylidene)- and N-(alkylidene)-homoallylamines are cyclised by electrophiles, e.g. bromine or phenylselenenyl bromide, and by subsequent reduction to the corresponding 3-functionalised pyrrolidines; the stereochemistry was investigated, and reductive removal of the 3(or 4)-bromo- and 3(or 4)-phenylseleno-substituents was accomplished.