PDF icon Download PDF
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
CrossrefPubMedSearch in Google Scholar
Further Information

Publication History

Publication Date:
16 May 2014 (online)

 
 PDF Download Permissions and Reprints

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.


 

 


  Permissions and Reprints