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SIAPhos: Phosphorylated Sulfonimidamides and their Use in Iridium‐Catalyzed Asymmetric Hydrogenations of Sterically Hindered Cyclic Enamides
Author(s) -
Patureau Frederic W.,
Worch Christin,
Siegler Maxime A.,
Spek Anthony L.,
Bolm Carsten,
Reek Joost N. H.
Publication year - 2012
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/adsc.201100692
Subject(s) - iridium , chemistry , steric effects , cationic polymerization , asymmetric hydrogenation , catalysis , medicinal chemistry , rhodium , chelation , phosphorylation , enantioselective synthesis , stereochemistry , organic chemistry , biochemistry
Phosphorylated sulfonimidamides (SIAPhos) undergo ion exchange reactions with cationic complexes, [Rh(cod) 2 BF 4 ] and [Ir(cod) 2 BarF], or neutral complexes [Rh(cod)Cl] 2 and [Ir(cod)Cl] 2 , leading to unprecedented neutral complexes with P‐N‐S‐N chelates. Use of the resulting neutral iridium complexes in asymmetric hydrogenation reactions of tri‐ and tetrasubstituted enamides leads to products with high enantioselectivities (up to 92% ee ).