Enantioselective RH-catalyzed hydrogenation of enol acetates and enol carbamates with monodentate phosphoramidites.
[reaction: see text] Monodentate phosphoramidites, in particular PipPhos and its octahydro analogue, are excellent ligands for the rhodium-catalyzed asymmetric hydrogenation of aromatic enol acetates, enol carbamates, and 2-dienol carbamates up to 98% ee. These latter substrates were hydrogenated selectively to the carbamates of the allyl alcohol.
Panella
Lavinia
L
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Feringa
Ben L
BL
de Vries
Johannes G
JG
Minnaard
Adriaan J
AJ
D000085:Acetates / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000085:Acetates; D002219:Carbamates; D009281:Naphthalenes; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D006859:Hydrogen; D012238:Rhodium