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An Efficient, Practical, and Enantioselective Method for Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst

Hao Wu, Fredrik Haeffner and Amir H. Hoveyda*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email:

H. Wu, F. Haeffner, A. H. Hoveyda, J. Am. Chem. Soc., 2014, 136, 3780-3781.

DOI: 10.1021/ja500374p

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Low loadings of an in situ generated B-based catalyst, that is derived from a simple, robust, and readily accessible chiral aminoalcohol, promote an enantioselective addition of an allene unit to aldimines. Various aryl-, heteroaryl-, and alkyl-substituted homoallenylamides can be obtained in very good yield and high enantiomeric excess at ambient temperature using a commercially available allenylboron reagent.

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Key Words

allenes, allylic amines

ID: J48-Y2014