Palladium-catalysed cascade ring expansion reaction of cyclobutanols that have a propargylic moiety with nucleophiles.
Palladium-catalysed cascade ring expansion reaction of cyclobutanols that have a propargylic moiety with nucleophiles.
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DOI：
10.1039/b410362a
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发表时间：
2004-10
影响因子：
3.2
通讯作者：
Masahiro Yoshida;Yuki Komatsuzaki;H. Nemoto*;M. Ihara*
中科院分区：
文献类型：
--
作者：
Masahiro Yoshida;Yuki Komatsuzaki;H. Nemoto*;M. Ihara*
本文描述了在钯催化剂作用下，含有多种丙叉基组份的四元环体系的级联环重排反应。具有丙烯酸碳酸酯部分的环丁醇与作为亲核剂的酚类反应，高产率地生成苯氧基诱导的环戊酮。这些反应以区域和非对映选择性的方式进行，以提供具有高选择性的取代环戊酮。亚胺也作为亲核剂来产生亚胺诱导的产物。丙戊基溴与醇钠成功地反应生成了相应的产物，产率很高。
Cascade ring rearrangement of four-membered ring systems containing various propargylic components by a palladium catalyst is described. The reactions of cyclobutanols that have a propargylic carbonate moiety with phenols as nucleophiles produce phenoxy-induced cyclopentanones in high yields. The reactions proceed in a regio- and diastereoselective manner to afford the substituted cyclopentanones with high selectivities. Imides also act as nucleophiles to produce the imidyl-induced products. Propargylic bromide successfully reacts with sodium alkoxides to produce the corresponding products in good yields.