Abbaspour Tehrani, Kourosch

Gadde, Karthik

Maes, Bert

Abstract: An efficient metal-free strategy for the synthesis of alpha-substituted homoallylamine derivatives has been developed via a 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-promoted 2-aza-Cope rearrangement of aldimines, generated in situ by condensation of aldehydes with easily accessible 1,1-diphenylhomoallylamines. This reaction provides rapid access to alpha-substituted homoallylamines with excellent functional group tolerance and yields. The reaction takes place at room temperature and no chromatographic purification is required for product isolation. The synthetic utility of the current method is further demonstrated by the transformation of the obtained benzophenone ketimines into N-unprotected homoallylamines, an alpha-amino alcohol and an alpha-amino amide

HFIP-mediated 2-aza-Cope rearrangement : metal-free synthesis of alpha-substituted homoallylamines at ambient temperature

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