Chemical and Pharmaceutical Bulletin p. 1439 - 1446 (1997)
Update date:2022-08-05
Topics:
Oda, Kozo
Yoshida, Akira
S[2(Dialkylaminocarbonyl)phenyl](2R)2[(3S,4S)3[(1R)1(tertbutyldimethylsilylox y)ethyl)]2oxo4azetidinyl]thiopropionate (11), useful intermediates for the synthesis of 1β-methylcarbapenems including 1β-methylthienamycin, were prepared in a highly stereoselective manner by the reaction of E-1-(tert- butyldimethyl-silyloxy)-1-[2-(dialkylaminocarbonyl)phenylthio]-1-propene (10) with commercially available (3S,4R)-3-[(1R)-1-(tert- butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (6) in the presence of zinc chloride catalyst. The diethylaminocarbonyl derivative (11b) was particularly convenient for practical production because of its highly crystalline nature.
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