Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 9, Pages 3210-3214Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b13563
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Funding
- European Research Council (ERC) [AdG 247014]
- Swedish Research Council [2016-03897]
- Berzelii Center EXSELENT
- Knut and Alice Wallenberg Foundation
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A highly diastereoselective palladium-catalyzed oxidative carbocyclization-borylation of enallenes assisted by a weakly coordinating hydroxyl group was developed. The reaction afforded functionalized cyclo-hexenol derivatives, in which the 1,3-relative stereo chemistry is controlled (d.r. > 50:1). Other weakly coordinating oxygen-containing groups (ketone, alkoxide, acetate) also assisted the carbocyclization toward cyclo-hexenes. The reaction proceeds via a ligand exchange on Pd of the weakly coordinating group with a distant olefin group. The high diastereoselectivity of the hydroxyl directed reaction could be rationalized by a face-selective coordination of the distant olefin. It was demonstrated that the primary coordination of the close-by oxygen containing functionality was necessary for the reaction to occur and removal of this functionality shut down the reaction.
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