Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 5, Pages 927-936Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901283
Keywords
Asymmetric catalysis; Organocatalysis; Michael addition; Enamine; Pyrrolidine
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The substitution of the 4-position of hydroxyproline by a phenol 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 alpha-functionalization of a wide range of linear/branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and alpha-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.
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