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Synfacts 2014; 10(6): 0623
DOI: 10.1055/s-0033-1341291
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Allene Addition to Aryl and Alkyl Imines

Contributor(s):
Paul Knochel
,
Diana Haas
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
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Further Information

Publication History

Publication Date:
16 May 2014 (online)

 
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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.


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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.


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