Enantioselective conjugate addition of ketones to β-nitrostyrenes catalyzed by 1,2-amino alcohol-derived prolinamides |
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| Institution: | 1. Siedlce University, Institute of Chemistry, 3 Maja 54, 08-110 Siedlce, Poland;2. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland;3. Institute of Physical Chemistry, Polish Academy of Science, Kasprzaka 44/52, 01-224 Warsaw, Poland;1. Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560012, India;2. Department of Applied Chemistry, Defence Institute of Advanced Technology, Girinagar, Pune 411025, India |
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| Abstract: | Various l-prolinamides 14, prepared from l-proline and chiral β-amino alcohols, are active bifunctional catalysts for the direct nitro-Michael addition of ketones to β-nitrostyrenes. In particular, catalyst 14e prepared from l-proline and (1S,2R)-cis-1-amino-2-indanol exhibits the highest catalytic performance working in polar aprotic solvents such as NMP. High syn-diastereoselectivities (up to 94% de) and good enantioselectivities (up to 80% ee) were obtained at rt. |
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