Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 19, Pages 10226-10233Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01731
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Funding
- National Natural Science Foundation of China [21372002, 21232007]
- PAPD
- Natural Science Foundation of Jiangsu Province [BK20160003]
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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 largescale reaction indicated that this catalytic asymmetric [3 + 2] cycloaddition could be scaled up for the synthesis of chiral cyclopenta[b]indole derivatives.
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