Wu H, Haeffner F, Hoveyda AH * Boston College, Chestnut Hill, USA
An Efficient, Practical, and Enantioselective Method for the Synthesis of Homoallenylamides
Catalyzed by an Aminoalcohol-Derived, Boron-Based Catalyst.
J. Am. Chem. Soc. 2014;
136: 3780-3783
Key words
allenes - boron - enantioselectivity
Significance
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.
Comment
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.
