Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons
Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons
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DOI：
10.1021/ol062882y
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发表时间：
2007-03-01
期刊：
影响因子：
5.2
通讯作者：
Murakami, Masahiro
中科院分区：
文献类型：
--
作者：
Miura, Tomoya;Harumashi, Tatsuro;Murakami, Masahiro
在铑（I）催化剂存在下，具有侧链氰基部分的不饱和酯与B-Ar-9-BBN反应，以良好的产率得到五元和六元β-烯氨基酯。通过Ar-铑（I）物质的初始共轭加成形成的（氧杂-π-烯丙基）铑（I）中间体经历与氰基的容易的分子内加成以构建碳环骨架。
Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered beta-enamino esters in good yield. An (oxa-pi-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.