Journal
ORGANIC LETTERS
Volume 23, Issue 24, Pages 9548-9553Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03780
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Funding
- National Natural Science Foundation of China [22001010]
- Anhui Provincial Natural Science Foundation [1908085QB55]
- Scientific Research Foundation of the Higher Education Institutions of Anhui Province [KJ2019A0499]
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The research has successfully developed an organocatalytic highly diastero- and enantioselective Friedel-Crafts conjugate addition method for adding indolizines to cyclopentenediones to obtain the desired products. The utility of the method was demonstrated through various late-stage functionalizations.
An organocatalytic highly diastero- and enantioselective Friedel-Crafts conjugate addition of indolizines to prochiral cyclopentenediones has been successfully developed. This desymmetric transformation provides a direct access to the desired indolizine-substituted cyclopentanediones in yields of 62-91% and excellent stereoselectivities. The utility of the approach was demonstrated by diverse late-stage functionalizations through reduction or oxidation. Importantly, the direct sp(2) C-H functionalization with nitromethane in one-pot process resulted in the indolizine-linked axially chiral styrene bearing a remote chiral center.
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