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Synlett 1992; 1992(1): 35-36
DOI: 10.1055/s-1992-21256
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Asymmetric Synthesis of Carbapenems Using Chiral Acetals: Synthesis of a Key Intermediate to (+)-PS-5

Hiromichi Fujioka* , Takeshi Yamanaka, Naoki Matsunaga, Masahiro Fuji, Yasuyuki Kita
  • *Faculty of Pharmaceutical Sciences, Osaka University, Yamada-oka 1-6, Suita, Osaka 565, Japan
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Publication Date:
18 September 2002 (online)

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Coupling reaction of the chiral imine acetal 5 [(4S,5S)-4,5-bis (methoxymethyl)-2- [(4-methoxyphenylimino)methyl]-2-(3-methoxyphenyl)-1, 3-dioxolane] and lithium enolate of methyl acetate proceeded in a highly diastereoselective manner to give ß-lactam 6. The reaction was applied to the synthesis of a key intermediate 11 [(2S,3R)-3-ethyl-4-oxo-2-azetidineacetic acid] to (+)-PS-5.