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.

引用

页码：2449 / 2451

页数：3

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