Journal
SCIENCE BULLETIN
Volume 65, Issue 7, Pages 557-563Publisher
ELSEVIER
DOI: 10.1016/j.scib.2020.01.017
Keywords
Umpolung gamma-addition; Amino acid-derived bifunctional phosphine; Allenoates; Mixed 3,3 '-Bisindole; Formal total syntheses
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Funding
- Singapore National Research Foundation, Prime Minister's Office for the NRF Investigatorship Award [R143-000-A15-281]
- National University of Singapore [R-143-000-695-114, C-141-000-092-001]
- National Natural Science Foundation of China [21672158]
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An enantioselective umpolung gamma-addition reaction of 3'-indolyl-3-oxindoles to allenoates catalyzed by amino acid-derived bifunctional phosphine catalysts has been developed. A wide range of chiral mixed 3,3'-bisindole scaffolds containing an all-carbon quaternary stereogenic center were obtained in high yields and with excellent enantioselectivities. 3,3'-Bisindoles are valuable synthetic intermediates, the employment of which led to formal total syntheses of (+)-Chimonanthine, (+)-Folicanthine and (-)-Calycanthine, as well as facile creation of useful pyrrolidinoindoline core structure. (C) 2020 Science China Press. Published by Elsevier B.V. and Science China Press. All rights reserved.
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