Hydroxy group directed chlorinolysis of (3S,4R)-3-[(R)-1-hydroxyethyl]-4-ethylthioazetidin-2-one (4) gives predominantly the corresponding (4S)-4-chloroazetidinone (5) which is cyclised to the (5R,6S)-6[(R)-1-hydroxyethyl]-2-thioxopenam (1).
N. Daniels, G. Johnson and B. C. Ross, J. Chem. Soc., Chem. Commun., 1983, 1006 DOI: 10.1039/C39830001006
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