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Substrate‐Controlled Diastereoselectivity Switch in Catalytic Asymmetric Direct Mannich Reaction of Glycine Derivatives with Imines: From anti ‐ to syn ‐α,β‐Diamino Acids
Author(s) -
HernándezToribio Jorge,
Gómez Arrayás Ramón,
Carretero Juan Carlos
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902258
Subject(s) - steric effects , glycine , aldimine , benzophenone , chemistry , catalysis , mannich reaction , substrate (aquarium) , combinatorial chemistry , sulfonyl , organic chemistry , stereochemistry , medicinal chemistry , amino acid , biochemistry , oceanography , alkyl , geology
Back and forth : A diastereoselectivity switch has been devised in the Fesulphos–Cu I ‐catalyzed glycine direct Mannich reaction with N ‐(8‐quinolyl)sulfonyl imines by tuning the steric and electronic properties of the glycine component (see scheme). α,β‐Diamino acids of syn configuration are produced under high diastereo‐ and enantiocontrol with glycinate esters derived from electron‐deficient benzophenone‐type ketimines, in contrast to aldimine‐derived pronucleophiles that lead to anti ‐configured products.