Stereoselective formation of carbon-carbon bonds via SN2-displacement: Synthesis of substituted cycloalkyl [b] indoles

…, D Zhao, EJJ Grabowski, AE McKeown…

Index: Hillier, Michael C.; Marcoux, Jean-Francois; Zhao, Dalian; Grabowski, Edward J. J.; McKeown, Arlene E.; Tillyer, Richard D. Journal of Organic Chemistry, 2005 , vol. 70, # 21 p. 8385 - 8394

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Citation Number: 42

Abstract

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 ...

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