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Synthesis 1997; 1997(1): 47-49
DOI: 10.1055/s-1997-1502
short paper
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A Facile Synthesis of (4S)-4-[(1R)-1-Carboxyethyl]-1-(tert-butyldimenthylsilyl)azetidin-2-one: A Key Intermediate of 1-β-Methylcarbapenems

Masahiko Seki, Tsutomu Miyake, Tatsuya Izukawa, Hiroshi Ohmizu*
  • *Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd., 3-16-89, Kashima, Yodogawa-ku, Osaka 532, Japan
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Publikationsdatum:
31. Dezember 2000 (online)

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Titanium enolate-mediated aldol-type reaction of the chiral N-propionyl-1,3-benzoxyzinone 4 with 4-acetoxyazetidin-2-one (5) gave the 2-(2-oxoazetidin-4-yl)propionic acid derivative 6 in high yield with high selectivity, which was transformed into (4S)-4-[(1R)-1-carboxyethyl]-1-(tert-butyldimethylsilyl)azetidin-2-one (3), a key intermediate of 1-β-methylcarbapenems 1.

A 1-β-methylcarbapenem key intermediate was conveniently prepared by the aldol-type reaction of chiral N-propionyl-1,3-benzoxazinone with 4-acetoxyazetidin-2-one