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Synfacts 2019; 15(08): 0879
DOI: 10.1055/s-0039-1689843
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective [4+4] Cycloadditions

Contributor(s):
Paul Knochel
,
Moritz Balkenhohl
Kennedy CR, Zhong H, Macaulay RL, Chirik PJ. * Princeton University, USA
Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes.

J. Am. Chem. Soc. 2019;
141: 8557-8573
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Publication History

Publication Date:
18 July 2019 (online)

 
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Key words

cycloaddition - diastereoselectivity - iron catalysis

Significance

Chirik and co-workers report a regio- and diastereoselective iron-catalyzed [4+4] cycloaddition of 1,3-dienes, leading to various substituted cyclooctadienes in excellent yields.


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Comment

Remarkably, with the choice of the iron catalyst, the cyclodimerization can be controlled in a diastereoselective fashion. Extensive mechanistic studies were performed and catalytically relevant iron complexes were isolated and characterized.


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