An unprecedented cleavage of the β-lactam ring: a novel synthesis of acyclic N, O-and N, S-acetals

Y Kita, N Shibata, N Kawano, N Yoshida…

Index: Kita, Yasuyuki; Shibata, Norio; Kawano, Noriyuki; Yoshida, Naoki; Matsumoto, Keita; Takebe, Yasushi Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 18 p. 2321 - 2329

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Citation Number: 13

Abstract

A new synthesis of acyclic,-acetals 3 and,-acetals 5 has been devised by way of a trimethylsilyl trifluoromethanesulfonate promoted formal 2, 3-bond fragmentation of 4- heteroatom substituted azetidinones 1 and 4, respectively. This reaction proceeds by nucleophilic attack of a nitrile group of the solvent on the c