TY - JOUR
T1 - Diastereoselective hydroformylation of Δ4-steroids with rhodium-phosphite catalysts
AU - Freixa, Zoraida
AU - Pereira, Mariette M.
AU - Bayón, J. Carles
AU - Silva, Artur M.S.
AU - Salvador, Jorge A.R.
AU - Beja, Ana Matos
AU - Paixão, José A.
AU - Ramos, Manuela
PY - 2001/5/8
Y1 - 2001/5/8
N2 - The hydroformylation of two steroidal substrates, namely 17β-acetoxyandrost-4-ene 1 and 3β,17β-diacetoxyandrost-4-ene 2, with a rhodium tris(O-tert-butylphenyl)phosphite catalyst was investigated. In both cases, the major reaction product was 4β-formyl-17β-acetoxy-5β-androstane 3, which was isolated and characterized by X-ray diffraction and NMR techniques. This reaction is the first example of catalytic carbonylation to the β face of a steroid backbone. The effect of reaction temperature, the pressure at which the reaction was completed and the ligand:Rh ratio on the regio- and stereoselectivity of the reaction is also discussed. © 2001 Elsevier Science Ltd.
AB - The hydroformylation of two steroidal substrates, namely 17β-acetoxyandrost-4-ene 1 and 3β,17β-diacetoxyandrost-4-ene 2, with a rhodium tris(O-tert-butylphenyl)phosphite catalyst was investigated. In both cases, the major reaction product was 4β-formyl-17β-acetoxy-5β-androstane 3, which was isolated and characterized by X-ray diffraction and NMR techniques. This reaction is the first example of catalytic carbonylation to the β face of a steroid backbone. The effect of reaction temperature, the pressure at which the reaction was completed and the ligand:Rh ratio on the regio- and stereoselectivity of the reaction is also discussed. © 2001 Elsevier Science Ltd.
U2 - 10.1016/S0957-4166(01)00191-4
DO - 10.1016/S0957-4166(01)00191-4
M3 - Article
SN - 0957-4166
VL - 12
SP - 1083
EP - 1087
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 7
ER -