Enantiomerically enriched homoallylamines and 3-allyl-3-hydroxy oxindoles are valuable synthetic intermediates in the synthesis of nitrogen containing small molecules. Utilizing the myriad transformations of the olefin present in these chiral compounds; heterocycles, bicycles, amino aldehydes, and many other alkaloid-like structures have been prepared and applied towards the synthesis of biologically active molecules. We introduce a new class of catalysts that allow for enantioselective additions of organoboronates to aldimines and isatins; these enantioselective and high yielding transformations are carried out at room temperature and in generally less that six hours with only 0.25-6 mol % catalyst loading. The catalyst itself has a molecular weight of 306 and is synthesized in 73% yield in four simple steps from abundant materials. We propose an internal hydrogen bond is critical for accelerating all steps of the catalytic cycle and allowing for high efficiencies without the use of a transition metal.

Simple organic molecules as catalysts for enantioselective synthesis of amines and alcohols

245th National Meeting (2013)

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