期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 22, 页码 10441-10449出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo301796r
关键词
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资金
- DST, India [SR/S1/OC-5/2012, SR/NM/NS-29/2010]
- CSIR, India
- UGC, India [F.PSW-121/10-11]
CeCl3 center dot 7H(2)O is found as an efficient catalyst for new intermolecular domino reactions of three-, four- and seven-component assemblies of common precursors under benign reaction conditions. Generation of enaminioesters from beta-keto esters and primary amines, activation of their allylic sp(3) C-H, vinylic sp(2) C-H and N-H bonds, multi C-C and C-N bond-forming cascade cyclization with 1,2-diketones and subsequent side-chain alkylation have been developed to construct functionalized pentasubstituted pyrroles and their chiral analogues. The scope of the domino reaction is successfully explored toward synthesis of highly aryl-substituted pyrroles, pentasubstituted pyrroles bearing C2-olefinic side-chain and spiro-2-pyrrolinones and their chiral analogues via unusual side-chain amination, elimination and ring contraction. The new domino reaction is operationally simple, robust, substrate specific, selective and high yielding.
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