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Synthesis of an optically active 4‐acetoxyazetidinone intermediate for penems and carbapenems
Author(s) -
Häbich Dieter,
Hartwig Wolfgang,
Born Liborius
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250225
Subject(s) - diastereomer , chemistry , stereochemistry , lactam , optically active , side chain , bicyclic molecule , ring (chemistry) , combinatorial chemistry , organic chemistry , polymer
The synthesis of the novel (3 R ,4 R )‐4‐acetoxy‐3‐[(1 S )‐1‐ t ‐ butyldimethylsilyloxymethyl‐1‐((1 S )‐1‐ phenylethylaminocarbonyl)]azetidin‐2‐one ( 1a ), a valuable key intermediate for penems and carbapenems bearing a 6‐hydroxyacetamide side chain, and its diastereomer 1b , from dimethyl cis ‐2,3‐oxirane dicarboxylate, is described. The allocation of absolute configurations to the diastereomers 1a and 1b ensued via single‐crystal X‐ray analysis of the isomer 1b.