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Easy approach to chiral Michael adducts by Eu +3 ‐catalyzed conjugate addition
Author(s) -
De Rosa Margherita,
Palombi Laura,
Acocella Maria Rosaria,
Fruilo Marina,
Villano Rosaria,
Soriente Annunziata,
Scettri Arrigo
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10246
Subject(s) - enantiopure drug , chemistry , conjugate , chirality (physics) , adduct , catalysis , epimer , michael reaction , addition reaction , medicinal chemistry , stereochemistry , enantioselective synthesis , organic chemistry , combinatorial chemistry , mathematical analysis , mathematics , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
Michael addition of enantiopure N‐acetoacetyl‐oxazolidin‐2‐ones is shown to take place in the presence of catalytic amounts of Eu +3 salts and complexes in high yields, very reduced reaction times, and moderate diastereoselectivity. The level of diastereoselectivity can be significantly enhanced by the suitable exploitation of the easy epimerization of the adducts in the presence of silica gel. Chirality 15:579–583, 2003. © 2003 Wiley‐Liss, Inc.