Diastereoselective hydroformylation of Δ4-steroids with rhodium-phosphite catalysts

Zoraida Freixa, Mariette M. Pereira, J. Carles Bayón, Artur M.S. Silva, Jorge A.R. Salvador, Ana Matos Beja, José A. Paixão, Manuela Ramos

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25 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)1083-1087
JournalTetrahedron Asymmetry
Volume12
Issue number7
DOIs
Publication statusPublished - 8 May 2001

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