Enantioselective Allene Addition to Aryl and Alkyl Imines

Paul Knochel; Diana Haas

doi:10.1055/s-0033-1341291

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Synfacts 2014; 10(6): 0623
DOI: 10.1055/s-0033-1341291

Metal-Mediated Synthesis

Enantioselective Allene Addition to Aryl and Alkyl Imines

Rezensent(en):

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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Publikationsverlauf

Publikationsdatum:
16. Mai 2014 (online)

Abstract
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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.

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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