890408-45-4Relevant articles and documents
Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H- indoles using trialkylboranes
Trost, Barry M.,Quancard, Jean
, p. 6314 - 6315 (2007/10/03)
We have developed a new enantioselective C-3 allylation of 3-substituted indoles using allyl alcohol and trialkylboranes. Asymmetric syntheses of 3,3-disubstituted indolines and indolenines in enantiomeric excesses up to 90% have been achieved using the bulky borane 9-BBN-C6H13 as the promoter of the reaction. The dependence of the selectivity on the nature of the borane suggests that the boron reagent has a role beyond promoting ionization of the allyl alcohol. A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine. Copyright