期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2019, 期 12, 页码 2234-2242出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201801709
关键词
Spiro compounds; Nucleophilic addition; Ambiphilicity; C-C coupling; Cycloaddition
资金
- Department of Science and Technology (DST), SERB, New Delhi [SB/FT/CS/079-2014]
A regioselective formal [4+2] cycloaddition reaction of nitrostyrene derived MBH alcohol and 2-arylidene-1,3-indanedione resulted in functionalized tetrahydrospiropyran derivatives with excellent chemical yields (up to 93 %). The reaction tolerated various electron rich and electron deficient substituents on the aryl group of 2-arylidene-1,3-indanedione as well as MBH alcohol. The utility of MBH alcohol as an ambident substrate, which is performing the dual role of nucleophile and electrophile with 2-arylidene-1,3-indanediones was successfully demonstrated for 20 derivatives. A single isomer was obtained exclusively in all the products via cascade process which followed an oxa-Michael-Michael addition sequence using cesium carbonate as base. Control experiments were carried out to understand the mechanistic details of the reaction. These experiments prove that the reaction undergoes a stepwise pathway rather than a concerted mechanism.
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