期刊
TETRAHEDRON
卷 67, 期 12, 页码 2206-2214出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.01.073
关键词
Cyclic hydroxamic acid; Intramolecular cyclization; Carbamate; Siderophore
资金
- National Institutes of Health under PHS [S06 GM08136, 1SC3GM084809-01]
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. (C) 2011 Elsevier Ltd. All rights reserved.
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