869194-38-7Relevant articles and documents
Stereoselective formation of carbon-carbon bonds via SN2- displacement: Synthesis of substituted cycloalkyl[b]indoles
Hillier, Michael C.,Marcoux, Jean-Francois,Zhao, Dalian,Grabowski, Edward J. J.,McKeown, Arlene E.,Tillyer, Richard D.
, p. 8385 - 8394 (2007/10/03)
A general asymmetric synthesis of substituted cycloalkyl[b]indoles has been accomplished. The key features of this approach are (1) the utilization of a Japp-Klingemann condensation/Fischer cyclization to prepare cycloalkyl[b] indolones, (2) the asymmetric borane reduction of these heterocyclic ketones with (S)-OAB to obtain enantiomerically pure alcohols, and (3) the stereoselective SN2-displacement of these indole alcohol substrates with a carbon nucleophile under Mitsunobu conditions to set the C1 or C3 tertiary carbon stereocenter. The use of trimethylphosphine (PMe3) and bis(2,2,2-trichloroethyl) azodicarboxylate (TCEAD) was found to have an effect on the Mitsunobu dehydrative alkylation.