Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives
Literature Information
Publication Date
2017-01-04
DOI
10.1039/C6QO00775A
Impact Factor
5.281
Authors
Zhusheng Huang, Qingqing Chen, Xiuqin Yang, Yang Liu, Li Zhang, Tao Lu, Qingfa Zhou
View Original
Abstract
A phosphine-mediated domino reaction between phthalimidomalonates and allenoates furnishes highly functionalized pyrroloisoindolinone derivatives in synthetically useful yields. When ethyl but-2-ynoate was reacted with phthalimidomalonates under the same conditions, pyrroloisoindolinone derivatives were also obtained in good to excellent yields. The mechanism for the transformation is a tandem γ-umpolung/Wittig/γ-umpolung process. The present domino reaction not only exploits the potential of allenoates, but also extends the existing phosphine-mediated cyclization scope.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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222723-55-9
Molecular Formula:
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