Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 23, Pages 3797-3808Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600931
Keywords
asymmetric organocatalysis; [3+2] cycloaddition; enantioselectivity; indolylmethanols; vinylindoles
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Funding
- National Natural Science Foundation of China [21372002, 21232007]
- Natural Science Foundation of Jiangsu Province [BK20160003]
- PAPD
- Graduate Students Project of JSNU
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The first catalytic asymmetric [3+2] cycloaddition of 2-indolylmethanols with 3-vinylindoles has been established, which makes use of C-3 unsubstituted 2-indolylmethanol as a C-3 building block in the presence of a chiral phosphoric acid. By using this strategy, biologically important cyclopenta[b]indole frameworks were efficiently constructed with regiospecificity in high yields (up to 99%), excellent diastereo- and enantioselectivities (up to >95:5 dr, 96:4 er). This reaction not only represents the first catalytic asymmetric [3+2] cycloaddition of C-3 unsubstituted 2-indolylmethanols, but also has confronted the great challenges in 2-indolylmethanol-involved enantioselective transformations.
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