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Synfacts 2005(1): 0166-0166  
DOI: 10.1055/s-2005-916022
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Proline-Based N-Oxides as Modular Chiral Catalysts for Allylation

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
J. F. Traverse, Y. Zhao, A. H. Hoveyda*, M. L. Snapper*
Boston College, USA
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

The authors introduce their modular amino acid based N-oxide as an organocatalyst for the allylation of aldehydes. The catalyst is prepared through a simple three-step route providing the N-oxide catalysts in good yield (˜50% for three steps). Good yields (>80%) and ee’s in the range of 71-92% are obtained for a number of aromatic aldehydes.