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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Diastereoselective Organocatalytic Michael Addition of 2-Arylacetates Having an Electron-Withdrawing Group to Nitroalkenes

Author(s): Sung-Gon Kim

Volume 9, Issue 8, 2012

Page: [572 - 576] Pages: 5

DOI: 10.2174/157017812802850168

Price: $65


The first efficient organocatalytic conjugate addition reaction of 2-arylacetates and 2-arylacetonitriles having an electron-withdrawing group to nitroalkenes has been achieved using a bifuctional amino thiourea catalyst. The reagents having NO2-, CO2Me-, and CN-functional groups on the aromatic ring can be used; the bifuctional catalyst 4i provided Michael adducts in the reaction of various nitroalkenes with broad generality in high yield and diastereoselectivity.

Keywords: Bifuctional catalyst, conjugate addition, Michael addition, nitroalkene, organocatalysis, pronucleophiles, carbon, stereogenic, alkaloid, acetate.

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