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Enantioselective Construction of Cyclopenta[b]indole Scaffolds via the Catalytic Asymmetric [3 + 2] Cycloaddition of 2-Indolylmethanols with p-Hydroxystyrenes
- Source :
- The Journal of Organic Chemistry. 82:10226-10233
- Publication Year :
- 2017
- Publisher :
- American Chemical Society (ACS), 2017.
-
Abstract
- The catalytic asymmetric [3 + 2] cycloaddition of 2-indolylmethanols to p-hydroxystyrenes was established in the presence of a chiral phosphoramide, and this reaction provided chiral cyclopenta[b]indole scaffolds in generally high yields and with good enantioselectivities (up to 98% yield, 99:1 er). The control experiments demonstrated that the dual hydrogen-bonding activation mode of the chiral catalyst toward the two substrates played an important role in the reaction. In addition, the large-scale reaction indicated that this catalytic asymmetric [3 + 2] cycloaddition could be scaled up for the synthesis of chiral cyclopenta[b]indole derivatives.
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 82
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....74c15c5b4478feee575e0da0753704bf