Application of a chiral scaffolding ligand in catalytic enantioselective hydroformylation.
The synthesis of β-amino-aldehydes has been achieved through enantioselective hydroformylation of PMP-protected allylic amines. The reaction is accomplished by using a scalemic scaffolding ligand that covalently and reversibly binds to the substrate. These ligands behave like chiral auxiliaries because they are covalently attached to the substrate during hydroformylation; however, similar to traditional asymmetric ligands, they can be used in catalytic quantities. The directed hydroformylation of disubstituted olefins occurs under mild conditions (35 °C and 50 psi CO/H(2)), and Z-olefins afford excellent enantioselectivities (up to 93% ee).
Worthy
Amanda D
AD
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Joe
Candice L
CL
Lightburn
Thomas E
TE
Tan
Kian L
KL
D002384:Catalysis; D005561:Formates / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D013237:Stereoisomerism
D005561:Formates; D008024:Ligands; C030544:formic acid