Are the 11-oxo-steroids really so hindered towards organometallic compounds?
Allylation of an 11-oxo-steroid, the protected adrenosterone, was studied to examine more closely the steric hindrance of such a ketosteroid. While the beta face exhibits, as well known, a strong steric hindrance, the alpha side appears to be only relatively hindered. A high diastereoselectivity was observed in the addition of crotyl magnesium bromide.
Lecomte
Vincent
V
Laboratoire de Chimie organométallique, Ecole Nationale Supérieure de Chimie et CNRS, 11 rue Pierre et Marie Curie, 75005 Paris, France.
Stéphan
Elie
E
Vaissermann
Jacqueline
J
Jaouen
Gérard
G
D000735:Androstenedione / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007664:Ketosteroids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D007664:Ketosteroids; D000735:Androstenedione