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Synfacts 2009(8): 0916-0916  
DOI: 10.1055/s-0029-1217594
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Conjugate Addition of Thioacetic Acid to Nitroalkenes

Contributor(s): Benjamin List, Steffen Müller
K. L. Kimmel, M. T. Robak, J. A. Ellman*
University of California, Berkeley, USA
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Publikationsverlauf

Publikationsdatum:
23. Juli 2009 (online)

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Significance

N-Sulfinyl urea 1 was identified as powerful organocatalyst for the conjugate addition of thioacetic acid to nitroalkenes. In cyclopentyl methyl ether (CPME) the desired products were obtained in good yields (÷63%) and high enantio­selectivities (er up to 98:2). The reaction tolerates a wide range of substrates including electron-rich and electron-deficient aromatic, as well as linear and branched aliphatic nitroalkenes.