Aziridines reaction with organocopper

Sn2 Reactions with epoxides and aziridines are also synthetically useful. An example of epoxide cleavage with an organocopper reagent with sp carbon moieties is the enantioselective synthesis of (3S, 4S)-4-methyl-3-heptanol (53), an elm bark beetle (Scolytus multistriatus) pheromone [42]. The chiral epoxy oxazolidine 51 [43], prepared from (R)-phenylglycinol, reacted with a propylmagnesium bromide-derived cuprate at —70 °C to afford the oxazolidine 52 in 74% yield (Scheme 9.12). Compound 52 was converted into the target molecular 53 by conventional procedures. 

Sn2 substitution reactions of alkyl halides with hard nucleophiles such as alkyl anions can be achieved most readily with the aid of organocopper chemistry [95]. Sn2 reactions with epoxides and aziridines are also synthetically useful [96]. The... 

Amino alcohols. By decomposition of allylic azidoformates to produce bicyclic oxazolidinone substrates for ring opening reactions, a stereoselective entry into jyn-1,2-amino alcohols is delineated. Thus, after treatment of the aziridines with organocopper species, trani-4,5-disubstituted oxazolidin-2-ones (14 examples, 55-91%) are obtained. 

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