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.
Davies
Huw M L
HM
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000, USA. hdavies@acsu.buffalo.edu
Jin
Qihui
Q
D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D003979:Diazonium Compounds; D009281:Naphthalenes; D009942:Organometallic Compounds; C407352:dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); D011392:Proline