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Synfacts 2022; 18(12): 1311
DOI: 10.1055/s-0042-1753065
Metals in Synthesis

Nickel-Catalyzed Enantioselective Multicomponent Reaction of 1,3-Dienes, Aldehydes, and Boronic Acids

Contributor(s):
Mark Lautens
,
Bijan Mirabi
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
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Key words

nickel catalysis - multicomponent reaction - 1,3-dienes

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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