Journal
ORGANIC LETTERS
Volume 23, Issue 9, Pages 3426-3431Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00810
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Funding
- Natural Science Foundation of China [21672048]
- Natural Science Foundation of Zhejiang Province [LY18B020015]
- Hangzhou Normal University
- Hangzhou City
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Iridium/Bronsted acid cooperative catalyzed asymmetric allylic substitution reactions at the C5 position of indolines have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products in good to high yields and enantioselectivities with wide functional group tolerance. The transformations not only enable the formation of C5-allylindoline derivatives, but also the synthesis of C5-allylindole analogues in good yields and excellent stereoselectivities via an allylation/oxidation reaction sequence.
Iridium/Bronsted acid cooperative catalyzed asymmetric allylic substitution reactions at the C5 position of indolines have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products in good to high yields (48-97%) and enantioselectivities (82% to >99% ee) with wide functional group tolerance. The transformations allow not only the formation of C5-allylindoline derivatives but also the synthesis of C5-allylindole analogues in good yields and excellent stereoselectivities via an allylation/oxidation reaction sequence.
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