Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes |
| |
Authors: | Trost Barry M Quancard Jean |
| |
Affiliation: | Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu |
| |
Abstract: | 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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|