Tetrahedron letters

Diastereoselective synthesis of a key intermediate for the preparation of tricyclic β-lactam antibiotics

T Matsumoto, T Murayama, S Mitsuhashi, T Miura

文献索引：Matsumoto, Takaji; Murayama, Toshiyuki; Mitsuhashi, Shigeru; Miura, Takashi Tetrahedron Letters, 1999 , vol. 40, # 27 p. 5043 - 5046

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被引用次数: 40

摘要

Asymmetric synthesis of (S)-5 has been accomplished with an excellent enantiomeric excess by hydrogenation of racemic 5 using ruthenium-BINAP-diamine-KOH system, followed by oxidation. Magnesium enolate of (2S)-2-methoxycyclohexanone [(S)-5] reacts with the 4-acetoxyazetidinone 4 to give the key intermediate 3 with high yield and diastereoselectivity for the synthesis of sanfetrinem 1.