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Synlett 1996; 1996(5): 455-456
DOI: 10.1055/s-1996-5463
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Practical Synthesis of Penems and Carbapenems Key Intermediate

Masahiko Seki, Tsutomu Miyake, Takeshi Yamanaka, Hiroshi Ohmizu*
  • *Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd., 16-89, Kashima-3-chome, Yodogawa-ku, Osaka 532, Japan
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Publication Date:
31 December 2000 (online)

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Titanium enolate-mediated aldol reaction of chiral N-phthaloyl-β-alanyl-1,3-benzoxazinone 5 with acetaldehyde furnished the (2S, 3R)-syn-aldol 6 in high yield with high stereoselectivity. Silylation of the hydroxy group of 6 followed by removal of the protective groups and cyclization gave the optically pure β-lactam 9 which was transformed into the acetoxyazetidinone 3, a key intermediate of penems and carbapenems.

acetoxyazetidinone - carbapenem - asymmetric aldol reaction

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