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Synfacts 2022; 18(12): 1311
DOI: 10.1055/s-0042-1753065
DOI: 10.1055/s-0042-1753065
Metals in Synthesis
Nickel-Catalyzed Enantioselective Multicomponent Reaction of 1,3-Dienes, Aldehydes, and Boronic Acids
Marcum JS,
Meek SJ.
*
University of North Carolina at Chapel Hill, USA
Efficient Enantio-, Diastereo-, E/Z-, and Site-Selective Nickel-Catalyzed Fragment Couplings of Aldehydes, Dienes, and Organoborons.
J. Am. Chem. Soc. 2022;
144: 19231-19237
DOI: 10.1021/jacs.2c08742.
Efficient Enantio-, Diastereo-, E/Z-, and Site-Selective Nickel-Catalyzed Fragment Couplings of Aldehydes, Dienes, and Organoborons.
J. Am. Chem. Soc. 2022;
144: 19231-19237
DOI: 10.1021/jacs.2c08742.
Significance
Marcum and Meek report a nickel-catalyzed multicomponent coupling reaction of aldehydes, 1,3-dienes, and arylboronic acids. The method is enantio-, diastereo-, and regioselective, affording the olefin products with extremely high E selectivity.
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Comment
The authors propose that the reaction initiates via an oxidative cyclization of the 1,3-diene and the aldehyde. Subsequent transmetalation with the arylboronic acid and reductive elimination yields the product. Mechanistic studies using D2O reveal no deuterium is incorporated.
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Publication History
Article published online:
17 November 2022
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