Asymmetric Addition of Aldehydes to Nitroalkenes with an
Immobilized Peptide

doi:10.1055/s-0030-1260898

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Synfacts 2011(9): 1026-1026
DOI: 10.1055/s-0030-1260898

Polymer-Supported Synthesis

Asymmetric Addition of Aldehydes to Nitroalkenes with an Immobilized Peptide

Contributor(s): Yasuhiro Uozumi, Go Hamasaka
Y. Arakawa, M. Wiesner, H. Wennemers*
University of Basel, Switzerland

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Publication History

Publication Date:
19 August 2011 (online)

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Significance

TentaGel-supported peptide 1 catalyzed the asymmetric conjugate addition of aldehydes 2 to nitroalkenes 3 to give the corresponding γ-nitro aldehydes 4 in 92-100% yield with a range of 37:1 to 99:1 syn/anti ratios and 92-97% ee (12 examples, eq. 1).