Journal of the American Chemical Society 2009-07-01

Enantioselective addition of thioacetic acid to nitroalkenes via N-sulfinyl urea organocatalysis.

Kyle L Kimmel, MaryAnn T Robak, Jonathan A Ellman

Index: J. Am. Chem. Soc. 131(25) , 8754-5, (2009)

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Abstract

The highly enantioselective addition of thioacetic acid to nitroalkenes using a new sulfinyl urea organocatalyst is described. The addition of thioacetic acid proceeds in high yields and enantioselectivities for a variety of aromatic and aliphatic nitroalkene substrates. This new method is useful for preparing chiral 1,2-aminothiol derivatives, as demonstrated by the first enantioselective synthesis of the clinically used antifungal drug sulconazole.