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Enantioselective double C-H activation of dihydronaphthalenes.

[reaction: see text] Dirhodium tetrakis((S)-N-dodecylbenzenesulfonyl)prolinate) (Rh2(S-DOSP)4) catalyzed reaction of 1,2-dihydronaphthalenes with an excess of methyl vinyldiazoacetates results in a formal double C-H activation, generating four new stereogenic centers with very high stereoselectivity. The mechanism of the C-H activation is complex, involving a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement.[1]

References

  1. Enantioselective double C-H activation of dihydronaphthalenes. Davies, H.M., Jin, Q. Org. Lett. (2005) [Pubmed]
 
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