Tetrahedron

A new approach to cyclic hydroxamic acids: intramolecular cyclization of N-benzyloxy carbamates with carbon nucleophiles

Y Liu, HK Jacobs, AS Gopalan

Index: Liu, Yuan; Jacobs, Hollie K.; Gopalan, Aravamudan S. Tetrahedron, 2011 , vol. 67, # 12 p. 2206 - 2214

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Citation Number: 12

Abstract

N-Alkyl-N-benzyloxy carbamates, 2, undergo facile intramolecular cyclization with a variety of carbon nucleophiles to give functionalized five-and six-membered protected cyclic hydroxamic acids, 3, in good to excellent yields. This method can be extended to prepare seven-membered cyclic hydroxamic acids in moderate yields. The sulfone intermediates 3 from this study can be alkylated while the corresponding phosphonates have been shown ...