Tantalum, like other early transition metals, has proven to be an effective catalyst for asymmetric intramolecular hydroamination of aminoallenes.  Previously, our group has studied titanium complexes of chiral amino alcohols, but these complexes gave low enantioselectivities up to 16 %ee. The use of tantalum precursors with the same alcohol ligands proved to give the desired pyrrolidine product in significantly higher enantioselectivity, up to 74 %ee of the (-) enantiomer, while retaining high conversions. Enantioselectivity was determined using chiral GC-MS. Experimental details and data trends for our new catalysts will be reported.

Catalytic hydroamination with tantalum complexes of chiral amino alcohols

239th National Meeting (2010)

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