Intramolecular Oxamidation of Unsaturated O-Alkyl Hydroxamates: A Remarkably Versatile Entry to Hydroxy Lactams

被引：123

作者：

Wardrop, Duncan J. ^{[1
]}

Bowen, Edward G. ^{[1
]}

Forslund, Raymond E. ^{[1
]}

Sussman, Adam D. ^{[1
]}

Weerasekera, Samanthi L. ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 04期

基金：

美国国家卫生研究院;

关键词：

N-ACYLNITRENIUM IONS; NITRENIUM ION; PHENYLIODINE(III) BIS(TRIFLUOROACETATE); ELECTROPHILIC ADDITION; FORMAL SYNTHESIS; ALKENES; CYCLIZATION; METHOXY; DECOMPOSITION; REACTIVITY;

D O I：

10.1021/ja9069997

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of a versatile method for the preparation of five- to eight-membered hydroxy lactams that involves the iodine(III)-mediated oxamidation of unsaturated O-alkyl hydroxamates is described. This transformation, which is believed to proceed through the intermediacy of singlet nitrenium and bicyclic N-acyl-N-alkoxyaziridinium ions, is both stereospecific and highly regioselective in most of the 22 cases examined.

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页码：1188 / +

页数：4

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