Efficient route to 2H-1,3-oxazines through ring expansion of isoxazoles by rhodium carbenoids

被引:68
作者
Manning, James R. [1 ]
Davies, Huw M. L. [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
isoxazole ring expansion; N-O insertion; rhodium carbenoid; aryldiazoacetates;
D O I
10.1016/j.tet.2008.03.010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Studies related to the total synthesis of elisabethin C led to the discovery of a rhodiurn-catalyzed cascade sequence involving isoxazole ring expansion and a [4+3] cycloaddition. The scope of the isoxazole ring expansion was explored, resulting in the synthesis of a range of 2H-1,3-oxazines in 47-96% yield. (C) 2008 Elsevier Ltd. All rights reserved.
引用
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页码:6901 / 6908
页数:8
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