Lewis acid-promoted hetero Diels-Alder cycloaddition of α-acetoxynitroso dienophiles

被引：49
|
作者：
Calvet, G [1 ]
Dussaussois, M [1 ]
Blanchard, N [1 ]
Kouklovsky, C [1 ]
机构：
[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, Lab Synth Substances Nat, F-91400 Orsay, France
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 14期
关键词：
D O I：
10.1021/ol0491336
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
alpha-Acetoxynitroso compound 3 has been prepared as a new stable, isolable, and reactive dienophile in nitroso Diels-Alder reactions. The yield of the [4 + 2] cycloaddition of alpha-acetoxynitroso dienophile with 1,3-dienes could be enhanced in the presence of 20 mol % Lewis acid. An unexpected retro hetero-Michael reaction from 26 was observed, leading to the cleavage of the N-O bond of the cycloadduct. This tandem nitroso Diels-Alder/retro hetero-Michael sequence has been used with cyclic and acyclic 1,3-dienes.
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收藏
页码：2449 / 2451
页数：3
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