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Scientific article
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Aminal-pyrrolidine organocatalysts - Highly efficient and modular catalysts for α-functionalization of carbonyl compounds

Published inEuropean journal of organic chemistry, no. 5, p. 927-936
Publication date2010
Abstract

The substitution of the 4-position of hydroxyproline by aphenol group, together with an aminal on the 2-position, gave a synergistic effect leading to two powerful complementary organocatalysts. They show excellent enantiocontrol in the -functionalization of a wide range of linear/branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and -amination. We obtained ees up to 98.5 % with low catalyst loadings (down to 1 mol-%). As a proof of efficiency, TOFs of up to 1000 h-1 could be obtained.

Keywords
  • Asymmetric catalysis
  • Organo­catalysis
  • Michael addition
  • Enamine
  • Pyrrolidine
Citation (ISO format)
QUINTARD, Adrien et al. Aminal-pyrrolidine organocatalysts - Highly efficient and modular catalysts for α-functionalization of carbonyl compounds. In: European journal of organic chemistry, 2010, n° 5, p. 927–936. doi: 10.1002/ejoc.200901283
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ISSN of the journal1099-0690
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