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DiPAMP’s Big Brother “ i‐ Pr‐SMS‐Phos” Exhibits Exceptional Features Enhancing Rhodium(I)‐Catalyzed Hydrogenation of Olefins
Author(s) -
Stephan Michel,
Šterk Damjan,
Mohar Barbara
Publication year - 2009
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.200900621
Subject(s) - chemistry , rhodium , diastereomer , phos , catalysis , adduct , medicinal chemistry , enol , ligand (biochemistry) , stereochemistry , organic chemistry , receptor , biochemistry
Switching Knowles DiPAMP’s {DiPAMP=1,2‐bis[( o ‐anisyl)(phenyl)phosphino]‐ ethane} MeO groups with i‐ PrO ones led to the i‐ Pr‐SMS‐Phos { i‐ Pr‐SMS‐Phos=1,2‐bis[( o ‐isoprop‐ oxyphenyl)(phenyl)phosphino]ethane} ligand which displayed a boosted catalyst activity coupled with an enhanced enantioselectivity in the rhodium(I)‐catalyzed hydrogenation of a wide‐range of representative olefinic substrates (dehydro‐α‐amido acids, itaconates, acrylates, enamides, enol acetates, α,α‐diarylethylenes, etc). The rhodium(I)‐( i‐ Pr‐SMS‐Phos) catalytic profile was investigated revealing its structural attributes and robustness, and in contrast to the usual trend, 31 P NMR analysis revealed that its methyl ( Z )‐α‐acetamidocinnamate (MAC) adduct consisted of a reversed diastereomeric ratio of 1.4:1 in favour of the most reactive diastereomer.