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Threonine‐Derived Phosphinite‐Oxazoline Ligands for the Ir‐Catalyzed Enantioselective Hydrogenation
Author(s) -
Menges Frederik,
Pfaltz Andreas
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200201)344:1<40::aid-adsc40>3.0.co;2-7
Subject(s) - chemistry , phosphinite , enantioselective synthesis , iridium , oxazoline , threonine , enantiomer , asymmetric hydrogenation , catalysis , serine , organic chemistry , enzyme
A series of chiral phosphinite‐oxazolines was synthesized in four steps starting from carboxylic acids and threonine methyl ester. In the asymmetric hydrogenation of a number of alkenes, iridium complexes of these ligands induced significantly higher enantioselectivities than the corresponding serine‐derived complexes. Enantiomeric excesses of 89 to 99% were obtained for unfunctionalized alkenes with turnover numbers of up to 5000.