Journal
SYNTHESIS-STUTTGART
Volume 50, Issue 2, Pages 295-302Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1590929
Keywords
dehydrative nucleophilic substitution; indole derivatives; azlactone; 2-indolylmethanol
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Funding
- NSFC [21372002, 21232007]
- Natural Science Foundation of Jiangsu Province [BK20160003, BK20170227]
- PAPD
- TAPP
- Undergraduate Student Project of Jiangsu province
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An efficient dehydrative nucleophilic substitution reaction of C3-substituted2-indolylmethanols with azlactones has been established. In the whole process, BrOnsted acid was supposed to activate two substrates simultaneously. A series of structurally diversified indole derivatives were obtained in generally good yields and high diastereoselectivities (up to 86% yield, >95:5 dr). This protocol not only provides a new strategy for the direct synthesis of structurally diversified indole derivatives, but also enriches the chemistry of 2-indolylmethanols via dehydrative substitution reaction.
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