Iron(III) Salt-Catalyzed Nazarov Cyclization/Michael Addition of Pyrrole Derivatives
Iron(III) Salt-Catalyzed Nazarov Cyclization/Michael Addition of Pyrrole Derivatives
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DOI：
10.1002/adsc.200800702
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发表时间：
2009-01-01
影响因子：
5.4
通讯作者：
Itoh, Toshiyuki
中科院分区：
文献类型：
--
作者：
Fujiwara, Masamune;Kawatsura, Motoi;Itoh, Toshiyuki
5摩尔%氧化铝负载的高氯酸铁[Fe(ClO4)(3)中心点Al_2O_3]能有效地催化两种吡咯衍生物的纳扎罗夫环化反应，具有较高的反式选择性和较好的产率。然后，在相同的铁盐存在下，环化产物与乙烯基酮反应，得到相应的Michael产品。4，5-二氢环戊酮[b]吡咯酮-6(1H)-酮衍生物5或5，6-二氢环戊酮-4(1H)-酮衍生物6的合成路线已在一种非常经济的铁催化剂上建立。
The Nazarov cyclization of two types of pyrrole derivatives was effectively catalyzed by 5 mol% alumina-supported iron(111) perchlorate [Fe(ClO4)(3)center dot Al2O3] which provided the desired cyclization with high trans selectivity in good to excellent yield. The cyclized product was next reacted with a vinyl ketone in the presence of the same iron salt to afford the corresponding Michael product. A sequential type Nazarov/Michael reaction of pyrrole derivatives has also been accomplished; the synthetic route to 4,5-dihydrocyclopenta[b]pyrrol-6(1H)-one derivative 5 or 5,6-dihydrocyclopenta[b]pyrrol-4(1H)-one derivative 6 has thus been established using a very economical iron catalyst.