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Synfacts 2009(9): 1038-1038  
DOI: 10.1055/s-0029-1217781
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Enantioselective Michael Addition to Nitroolefins in Water

Contributor(s): Benjamin List, Steffen Müller
J. Wu, B. Ni*, A. Headley*
Texas A&M University-Commerce, USA
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Publikationsdatum:
21. August 2009 (online)

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Significance

The new di(methylimidazole)prolinol silyl ether (1), a water soluble organocatalyst, was found to efficiently promote the conjugate addition of aldehydes to nitroolefins in aqueous solution. The reaction between aliphatic aldehydes and ­aromatic nitroalkenes in brine in the presence of 1 and sodium bicarbonate gave the corresponding Michael adducts in moderate to high yields and excellent enantioselectivities (er up to 99.5:0.5).