C-H activation as a strategic reaction: enantioselective synthesis of 4-substituted indoles.
A method is described for the asymmetric synthesis of 4-substituted indoles from the Rh2(S-DOSP)4-catalyzed decomposition of vinyldiazoacetates in the presence of N-Boc-4-acetoxy-6,7-dihydroindole. The reaction proceeds via a combined C-H activation/Cope rearrangement-elimination mechanism resulting in good yields and very high asymmetric induction.
Davies
Huw M L
HM
Department of Chemistry, University at Buffalo, The State University of New York, 14260-3000, USA. hdavies@buffalo.edu
Manning
James R
JR
D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; D009942:Organometallic Compounds; C407352:dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); D011392:Proline