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  • Title: Rhodium-mediated enantioselective cyclopropanation of allenes.
    Author: Gregg TM, Farrugia MK, Frost JR.
    Journal: Org Lett; 2009 Oct 01; 11(19):4434-6. PubMed ID: 19711905.
    Abstract:
    Reaction of monosubstituted allenes with aryldiazoacetate esters under dirhodium tetracarboxylate catalysis led to alkylidene cyclopropane products in 80-90% ee. Monosubstituted alkyl- and arylallene substrates gave 60-75% yield under standard conditions, while yields for 1,1-disubstituted allenes were significantly lower. Cyclopropanation of 1-methyl-1-(trimethylsilyl)allene proceeded in higher yield than other 1,1-disubstituted substrates, suggesting rate enhancement mediated by a significant beta-silicon effect.
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