Stereoselective synthesis of new beta-lactams by cyclocondensation of 1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene with 4-formyl substituted azetidinones.
The BF3.OEt2 or LiClO4 catalyzed hetero Diels-Alder reaction of 1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (Danishefsky's diene) with enantiomerically pure 4-formylazetidin-2-ones affords the corresponding cycloadducts in fair to good yields and in diastereoisomeric ratios of up to 98:2.
Annunziata
R
R
Centro CNR, Universitá degli Studi di Milano, Italy.
Benaglia
M
M
Cinquini
M
M
Cozzi
F
F
Montanari
F
F
Raimondi
L
L
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001384:Azetidines / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams
D000900:Anti-Bacterial Agents; D001384:Azetidines; D002070:Butadienes; D047090:beta-Lactams