Diastereoselective hydroformylation of Delta(4)-steroids with rhodium-phosphite catalysts

Citation
Z. Freixa et al., Diastereoselective hydroformylation of Delta(4)-steroids with rhodium-phosphite catalysts, TETRAHEDR-A, 12(7), 2001, pp. 1083-1087
Citations number
25
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
0957-4166 → ACNP
Volume
12
Issue
7
Year of publication
2001
Pages
1083 - 1087
Database
ISI
SICI code
0957-4166(20010508)12:7<1083:DHODWR>2.0.ZU;2-G
Abstract
The hydroformylation of two steroidal substrates, namely 17 beta -acetoxyan drost-4-ene 1 and 3 beta, 17 beta -diacetoxyandrost-4-ene 2, with a rhodium tris(O-tert-butylphenyl)phosphite catalyst was investigated. In both cases , the major reaction product was 4 beta -formyl-17 beta -acetoxy-5 beta -an drostane 3, which was isolated and characterized by X-ray diffraction and N MR techniques. This reaction is the first example of catalytic carbonylatio n to the beta face of a steroid backbone. The effect of reaction temperatur e, the pressure at which the reaction was completed and the ligand:Rh ratio on the regio- and stereoselectivity of the reaction is also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.