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

作者：Liu Yuan; Jacobs Hollie K; Gopalan Aravamudan S^*

来源：Tetrahedron, 2011, 67(12): 2206-2214.

DOI：10.1016/j.tet.2011.01.073

• Cyclic hydroxamic acid
• Intramolecular cyclization
• Carbamate
• Siderophore

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 to undergo HWE reaction. The alpha,beta-unsaturated synthon, 8, prepared by thermal elimination of sulfoxide 3m, undergoes Michael addition with secondary amines. The usefulness of this approach to prepare polydentate chelators has been demonstrated by the synthesis of bis cyclic hydroxamic acids 12, 14, and 15.

• 出版日期2011-3-25