Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 22, Pages 5600-5603Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310905
Keywords
amination; asymmetric catalysis; cyclization; phase-transfer catalysis; photolysis
Categories
Funding
- NIHGMS [R01 GM104534]
- UNCF
- Merck
- Amgen Foundation
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Herein is reported the first asymmetric utilization of aryldiazonium cations as a source of electrophilic nitrogen. This is achieved through a chiral anion phase-transfer pyrroloindolinization reaction that forms C3-diazenated pyrroloindolines from simple tryptamines and aryldiazonium tetrafluoroborates. The title compounds are obtained in up to 99% yield and 96% ee. The air-and water-tolerant reaction allows electronic and steric diversity of the aryldiazonium electrophile and the tryptamine core.
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