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Iron-Catalyzed Highly Regio- and Stereoselective Conjugate Addition of 2,3-Allenoates with Grignard Reagents
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Section:Abstract
An efficient highly regio- and stereoselective iron-catalyzed conjugate addition of 2,3-allenoates with primary or secondary alkyl, phenyl, or vinyl Grignard reagents to synthesize multi-substituted β,γ-unsaturated enoates has been reported. The in situ formed magnesium dienolate may readily react with different electrophilic reagents to construct an allylic quaternary carbon at the α-position of the ester group.
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This article has been cited by 13 ACS Journal articles (5 most recent appear below).
Efficient Assembly of Chromone Skeleton from 2,3-Allenoic Acids and Benzynes
Guobi Chai, Youai Qiu, Chunling Fu, and Shengming MaOrganic Letters2011 13 (19), 5196-5199Efficient Assembly of Chromone Skeleton from 2,3-Allenoic Acids and Benzynes
Guobi Chai, Youai Qiu, Chunling Fu, and Shengming MaOrganic Letters2011 13 (19), 5196-5199Chromone derivatives were synthesized from 2,3-allenoic acids and benzynes in moderate to excellent yields under mild conditions. Instead of the cyclic conjugate addition of the intermediate A formed by the nucleophilic addition of allenoic acid with ...
A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs
Guobi Chai, Shangze Wu, Chunling Fu, and Shengming MaJournal of the American Chemical Society2011 133 (11), 3740-3743A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs
Guobi Chai, Shangze Wu, Chunling Fu, and Shengming MaJournal of the American Chemical Society2011 133 (11), 3740-3743An efficient method for synthesis of polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain, is described. The reaction of 2,3-allenoates and organozinc reagents proceeds via a tandem ...
Iron-Catalyzed Domino Process for the Synthesis of α-Carbonyl Furan Derivatives via One-Pot Cyclization Reaction
Huanfeng Jiang, Wenjuan Yao, Hua Cao, Huawen Huang and Derong CaoThe Journal of Organic Chemistry2010 75 (15), 5347-5350Iron-Catalyzed Domino Process for the Synthesis of α-Carbonyl Furan Derivatives via One-Pot Cyclization Reaction
Huanfeng Jiang, Wenjuan Yao, Hua Cao, Huawen Huang and Derong CaoThe Journal of Organic Chemistry2010 75 (15), 5347-5350The Fe(ClO4)3-catalyzed intramolecular rearrangement/cyclization/oxidation reaction sequence for the synthesis of α-carbonyl furan derivatives from electron-deficient alkynes and 2-yn-1-ols is reported.
Iron-Promoted Synthesis of Substituted 1-Halo-1,4-pentadienes by Reaction of 1,3-Diarylpropenes with Ethynylbenzenes via sp3 C−H Bond Activation
Hanjie Mo and Weiliang BaoThe Journal of Organic Chemistry2010 75 (14), 4856-4859Iron-Promoted Synthesis of Substituted 1-Halo-1,4-pentadienes by Reaction of 1,3-Diarylpropenes with Ethynylbenzenes via sp3 C−H Bond Activation
Hanjie Mo and Weiliang BaoThe Journal of Organic Chemistry2010 75 (14), 4856-4859An iron-promoted sp3 C−H bond activation and C−C bond formation reaction between 1,3-diarylpropenes and ethynylbenzenes was realized with BQ (benzoquinone) as an oxidant. The reaction afforded 1-halo-1,4-pentadiene derivatives in moderate to good yields ...
Iron-Catalyzed Tandem Oxidative Coupling and Annulation: An Efficient Approach to Construct Polysubstituted Benzofurans
Xingwei Guo, Rong Yu, Haijun Li and Zhiping LiJournal of the American Chemical Society2009 131 (47), 17387-17393Iron-Catalyzed Tandem Oxidative Coupling and Annulation: An Efficient Approach to Construct Polysubstituted Benzofurans
Xingwei Guo, Rong Yu, Haijun Li and Zhiping LiJournal of the American Chemical Society2009 131 (47), 17387-17393The combination of FeCl3·6H2O and di-tert-butyl peroxide offers a novel and efficient method for the construction of polysubstituted benzofurans 3 from the reaction of simple phenols 1 and β-keto esters 2, which are expected to give coumarins in the well-...
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History
- Published In Issue November 28, 2007
- Received August 1, 2007
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