Lanthanide Triflate Catalysed Reactions of Acetals with Primary Amines and Cascade Cyclisation Reactions

Harry Heaney; Michael T. Simcox; Alexandra M. Z. Slawin; Robert G. Giles

doi:10.1055/s-1998-1734

Synlett 1998; 1998(6): 640-642
DOI: 10.1055/s-1998-1734

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Lanthanide Triflate Catalysed Reactions of Acetals with Primary Amines and Cascade Cyclisation Reactions

Harry Heaney^* , Michael T. Simcox, Alexandra M. Z. Slawin, Robert G. Giles

^*Department of Chemistry, Loughborough University, Loughborough, Leicestershire, LE11 3TU; Fax + 44(15 09)22 39 25; E-mail: h.heaney@lboro.ac.uk

Abstract

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The formation of imines from acetals and primary amines can be carried out at significantly lower temperatures using scandium or lanthanide triflates as catalysts, than in the absence of a catalyst: the intermediate aminol ethers can also take part in cascade cyclisation reactions, for example using tryptamine and ethyl tryptophanate.

acetal - re-usable catalyst - diastereoselectivity - imine - isoindolone

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