Diastereoselective Carbocyclization of 1,6‐Heptadienes Triggered by Rhodium‐Catalyzed Activation of an Olefinic CH Bond |
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Authors: | Dr. Christophe Aïssa Kelvin Y. T. Ho Dr. Daniel J. Tetlow María Pin‐Nó |
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Affiliation: | Department of Chemistry, University of Liverpool, Crown Street, L69 7ZD (UK) |
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Abstract: | The use of α,ω‐dienes as functionalization reagents for olefinic carbon–hydrogen bonds has been rarely studied. Reported herein is the rhodium(I)‐catalyzed rearrangement of prochiral 1,6‐heptadienes into [2,2,1]‐cycloheptane derivatives with concomitant creation of at least three stereogenic centers and complete diastereocontrol. Deuterium‐labeling studies and the isolation of a key intermediate are consistent with a group‐directed C? H bond activation, followed by two consecutive migratory insertions, with only the latter step being diastereoselective. |
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Keywords: | C H activation diastereoselectivity diene rearrangement rhodium |
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