Synthesis of N-containing organic molecules in high enantiomeric purity is crucial to chemistry, biology and medicine. Despite of some ground-breaking investigations, a general protocol for efficient and enantioselective synthesis of homoallenylamines still needs to be developed. Here, we have disclosed a metal-free catalytic method for enantioselective addition of an allene unit to Boc-aldimines, catalyzed by an in-situ generated B-based catalyst, which is derived from a simple, robust and readily accessible (in mutigram quantities) chiral aminoalcohol. A range of aryl-, heteroaryl- as well as alkyl-substituted homoallenylamides can be obtained in 66-91% yield and 84:16 to >99:1 er through reactions performed at room temperature and in the presence of 0.1-3.0 mol % of the chiral catalyst. The reactions don't require strict anhydrous conditions and can be performed on gram scale. The utility of this protocol is demonstrated through the synthesis of anisomycin and ?epi-cytoxazone.

Efficient, practical, and enantioselective method for synthesis of homoallenylamides catalyzed by an aminoalcohol-derived boron-based catalyst

248th National Meeting (2014)

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