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Enantioselective Allene Addition to Aryl and Alkyl Imines
An Efficient, Practical, and Enantioselective Method for the Synthesis of Homoallenylamides Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst.
J. Am. Chem. Soc. 2014;
16 May 2014 (online)
Hoveyda and co-workers report a highly efficient method for the enantioselective preparation of aryl-, heteroaryl-, and alkyl-substituted homoallenylamides. The addition of an allenyl unit to various Boc-protected imines proceeds with high yield and very good enantioselectivity.
The application of this new protocol shows its relevance in the total syntheses of the natural products anisomycin and epi-cytoxazone. Furthermore, it is shown that the allenyl addition performed on gram scale proceeds with high efficiency and selectivity, providing the corresponding product in excellent yield.