Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 13, Issue 10, Pages 1327-1334Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201800300
Keywords
alkylation; asymmetric synthesis; indoles; Mannich reaction; synthetic methods
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Funding
- UGC, New Delhi
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An asymmetric aza-Friedel-Crafts alkylation reaction between indoles and indolenines that were derived insitu from 3-indolinone-2-carboxylates has been developed by using 3,3-bis(triphenylsilyl)-1,1-binaphthyl-2,2-diyl hydrogen phosphate as a catalyst. The reaction proceeded under mild conditions and provided chiral indol-3-yl-3-indolinone-2-carboxylate derivatives in good yields with excellent ee values (up to 98.6%). Similarly, the Mannich-type addition of indoline-3-ones to indolenines provided heterodimers with vicinal chiral quaternary centers. This method was successfully applied to the construction of the core structure of trigonoliimineC.
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